Novel compound, organic electroluminescence device and electronic apparatus

ABSTRACT

A compound having structures represented by the following formulas (1) or (2): wherein in the formulas (1) and (2), at least one of R 1  to R 8  is a deuterium atom.

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a continuation of U.S. patent applicationSer. No. 17/282,347, filed on Apr. 1, 2021, which claims priority under37 U.S.C. § 371 to International Patent Application No.PCT/JP2019/039846, filed Oct. 9, 2019, which claims priority to and thebenefit of U.S. patent application Ser. No. 16/557,675, filed on Aug.30, 2019, and U.S. patent application Ser. No. 16/593,743, filed on Oct.4, 2019, and Japanese Patent Application No. 2019-101578, filed on May30, 2019, and Japanese Patent Application No. 2019-101675, filed on May30, 2019, and Japanese Patent Application No. 2018-191224, filed on Oct.9, 2018, and Japanese Patent Application No. 2018-190838, filed on Oct.9, 2018. The contents of these applications are hereby incorporated byreference in their entireties.

TECHNICAL FIELD

The invention relates to a new compound, an organic electroluminescencedevice and an electronic apparatus.

BACKGROUND ART

When a voltage is applied to an organic electroluminescence device(hereinafter may be referred to as an organic EL device), holes areinjected to an emitting layer from an anode and electrons are injectedto an emitting layer from a cathode. In the emitting layer, injectedholes and electrons are re-combined and excitons are formed.

Although materials for an organic EL device are being improved graduallyto increase the performances of the organic EL device (for example,Patent Documents 1 to 9), high performances are further offered. Inparticular, improvement in lifetime of an organic EL device is animportant task relating to a lifetime of commercial products providedwith the organic EL device, and thus a material enabling to realize along-lifetime organic EL device is required.

RELATED ART DOCUMENTS Patent Documents

-   Patent Document 1: WO2017/023021-   Patent Document 2: WO2013/106041-   Patent Document 3: Publication of US Patent Application No.    20170025608-   Patent Document 4: WO2017/023021-   Patent Document 5: JP-A-2006-151844-   Patent Document 6: WO2010/099534-   Patent Document 7: WO2010/135395-   Patent Document 8: WO2010/071362-   Patent Document 9: WO2010/066830

SUMMARY OF THE INVENTION

An object of the invention is to provide a compound capable of producingan organic EL device having a long lifetime, an organic EL device havinga long lifetime and an electronic apparatus provided with the organic ELdevice.

As a result of extensive studies, the inventors have found that anorganic EL device having a long lifetime can be obtained by usingcompounds having a specific structure represented by formula (1) or (2),and they have achieved the invention.

According to the invention, the following compound, organic EL deviceand electric apparatus can be provided.

1. A compound having structures represented by the following formulas(1) or (2):

wherein in the formulas (1) and (2),

R₁ to R₈ and R₁₁ to R₁₄ are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

R₁₅ to R₁₈ are hydrogen atoms;

R₉₀₁ to R₉₀₇ are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

when two or more of R₉₀₁ to R₉₀₇ exist, two or more of R₉₀₁ to R₉₀₇ maybe the same with or different from each other;

at least one of R₁ to R₈ is a deuterium atom;

two or more adjacent groups of R₁ to R₄, two or more adjacent groups ofR₅ to R₈ and two or more adjacent groups of R₁₁ to R₁₄ do not form aring;

L₁ and L₂ are independently

a single bond,a substituted or unsubstituted arylene group having 6 to 30 ring carbonatoms, ora substituted or unsubstituted divalent heterocyclic group having 5 to30 ring atoms;

Ar is

a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms.2. An organic electroluminescence device comprising:

a cathode, an anode, and one or two or more organic layer disposedbetween the cathode and the anode, wherein at least one organic layercomprises the compound according to the above 1.

3. An electronic apparatus provided with the organic electroluminescencedevice according to the above 2.

According to the invention, a compound capable of producing an organicEL device having a long lifetime, an organic EL device having a longlifetime, and an electronic apparatus provided with the organic ELdevice can be provided.

MODE FOR CARRYING OUT THE INVENTION Definition

In this specification, a hydrogen atom means an atom including isotopesdifferent in the number of neutrons, namely, a protium, a deuterium anda tritium.

In this specification, to a bondable position in which a symbol such as“R”, or “D” representing a deuterium atom is not specified in a chemicalformula, a hydrogen atom, that is, a light hydrogen atom, a deuteriumatom, or a tritium atom is bonded thereto.

In this specification, a term “ring carbon atoms” represents the numberof carbon atoms among atoms forming a subject ring itself of a compoundhaving a structure in which atoms are bonded in a ring form (forexample, a monocyclic compound, a fused ring compound, a cross-linkedcompound, a carbocyclic compound or a heterocyclic compound). When thesubject ring is substituted by a substituent, the carbon contained inthe substituent is not included in the number of ring carbon atoms. Thesame shall apply to the “ring carbon atoms” described below, unlessotherwise noted. For example, a benzene ring has 6 ring carbon atoms, anaphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ringcarbon atoms, and a furan ring has 4 ring carbon atoms. Further, forexample, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a9,9′-spirobifluorenyl group has 25 ring carbon atoms.

Further, when the benzene ring or the naphthalene ring is substituted byan alkyl group as a substituent, for example, the number of carbon atomsof the alkyl group is not included in the ring carbon atoms.

In this specification, a term “ring atoms” represents the number ofatoms forming a subject ring itself of a compound having a structure inwhich atoms are bonded in a ring form (for example, a monocycle, a fusedring and a ring assembly) (for example, a monocyclic compound, a fusedring compound, a cross-linked compound, a carbocyclic compound or aheterocyclic compound). The term “ring atoms” does not include atomswhich do not form the ring (for example, a hydrogen atom whichterminates a bond of the atoms forming the ring) or atoms contained in asubstituent when the ring is substituted by the substituent. The sameshall apply to the “ring atoms” described below, unless otherwise noted.For example, a pyridine ring has 6 ring atoms, a quinazoline ring has 10ring atoms, and a furan ring has 5 ring atoms. A hydrogen atom bondedwith a carbon atom of the pyridine ring or the quinazoline ring or anatom forming the substituent is not included in the number of the ringatoms.

In this specification, a term “XX to YY carbon atoms” in an expressionof “substituted or unsubstituted ZZ group including XX to YY carbonatoms” represents the number of carbon atoms when the ZZ group isunsubstituted. The number of carbon atoms of a substituent when the ZZgroup is substituted is not included. Here, “YY” is larger than “XX”,and “XX” and “YY” each mean an integer of 1 or more.

In this specification, a term “XX to YY atoms” in an expression of“substituted or unsubstituted ZZ group including XX to YY atoms”represents the number of atoms when the ZZ group is unsubstituted. Thenumber of atoms of a substituent when the group is substituted is notincluded. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean aninteger of 1 or more.

A term “unsubstituted” in the case of “substituted or unsubstituted ZZgroup” means that the ZZ group is not substituted by a substituent, anda hydrogen atom is bonded therewith. Alternatively, a term “substituted”in the case of “substituted or unsubstituted ZZ group” means that one ormore hydrogen atoms in the ZZ group are substituted by a substituent.Similarly, a term “substituted” in the case of “BB group substituted byan AA group” means that one or more hydrogen atoms in the BB group aresubstituted by the AA group.

Hereinafter, the substituent described herein will be described.

The number of the ring carbon atoms of the “unsubstituted aryl group”described herein is 6 to 50, preferably 6 to 30, and more preferably 6to 18, unless otherwise specified.

The number of the ring carbon atoms of the “unsubstituted heterocyclicgroup” described herein is 5 to 50, preferably 5 to 30, and morepreferably 5 to 18, unless otherwise specified.

The number of the carbon atoms of the “unsubstituted alkyl group”described herein is 1 to 50, preferably 1 to 20, and more preferably 1to 6, unless otherwise specified.

The number of the carbon atoms of the “unsubstituted alkenyl group”described herein is 2 to 50, preferably 2 to 20, and more preferably 2to 6, unless otherwise specified.

The number of the carbon atoms of the “unsubstituted alkynyl group”described herein is 2 to 50, preferably 2 to 20, and more preferably 2to 6, unless otherwise specified.

The number of the ring carbon atoms of the “unsubstituted cycloalkylgroup” described herein is 3 to 50, preferably 3 to 20, and morepreferably 3 to 6, unless otherwise specified.

The number of the ring carbon atoms of the “unsubstituted arylene group”described herein is 6 to 50, preferably 6 to 30, and more preferably 6to 18, unless otherwise specified.

The number of the ring atoms of the “unsubstituted divalent heterocyclicgroup” described herein is 5 to 50, preferably 5 to 30, and morepreferably 5 to 18, unless otherwise specified.

The number of the carbon atoms of the “unsubstituted alkylene group”described herein is 1 to 50, preferably 1 to 20, and more preferably 1to 6, unless otherwise specified.

Specific examples (specific example group G1) of the “substituted orunsubstituted aryl group” described herein include an unsubstituted arylgroup and a substituted aryl group described below. (Here, a term“unsubstituted aryl group” refers to a case where the “substituted orunsubstituted aryl group” is the “unsubstituted aryl group,” and a term“substituted aryl group” refers to a case where the “substituted orunsubstituted aryl group” is the “substituted aryl group”. Hereinafter,a case of merely “aryl group” includes both the “unsubstituted arylgroup” and the “substituted aryl group”.

The “substituted aryl group” refers to a case where the “unsubstitutedaryl group” has a substituent, and specific examples thereof include agroup in which the “unsubstituted aryl group” has the substituent, and asubstituted aryl group described below. It should be noted that examplesof the “unsubstituted aryl group” and examples of the “substituted arylgroup” listed herein are only one example, and the “substituted arylgroup” described herein also includes a group in which a group in which“unsubstituted aryl group” has a substituent further has a substituent,and a group in which “substituted aryl group” further has a substituent,and the like.

An unsubstituted aryl group:

a phenyl group,a p-biphenyl group,a m-biphenyl group,an o-biphenyl group,a p-terphenyl-4-yl group,a p-terphenyl-3-yl group,a p-terphenyl-2-yl group,a m-terphenyl-4-yl group,a m-terphenyl-3-yl group,a m-terphenyl-2-yl group,an o-terphenyl-4-yl group,an o-terphenyl-3-yl group,an o-terphenyl-2-yl group,a 1-naphthyl group,a 2-naphthyl group,an anthryl group,a benzanthryl group,a phenanthryl group,a benzophenanthryl group,a phenalenyl group,a pyrenyl group,a chrysenyl group,a benzochrysenyl group,a triphenylenyl group,a benzotriphenylenyl group,a tetracenyl group,a pentacenyl group,a fluorenyl group,a 9,9′-spirobifluorenyl group,a benzofluorenyl group,a dibenzofluorenyl group,a fluoranthenyl group,a benzofluoranthenyl group, anda perylenyl group.

A substituted aryl group:

an o-tolyl group,a m-tolyl group,a p-tolyl group,a p-xylyl group,a m-xylyl group,an o-xylyl group,a p-isopropyl phenyl group,a m-isopropyl phenyl group,an o-isopropyl phenyl group,a p-t-butylphenyl group,a m-t-butylphenyl group,an o-t-butylphenyl group,a 3,4,5-trimethylphenyl group,a 9,9-dimethylfluorenyl group,a 9,9-diphenylfluorenyl groupa 9,9-di(4-methylphenyl)fluorenyl group,a 9,9-di(4-isopropylphenyl)fluorenyl group,a 9,9-di(4-t-butylphenyl)fluorenyl group,a cyanophenyl group,a triphenylsilylphenyl group,a trimethylsilylphenyl group,a phenylnaphthyl group, anda naphthylphenyl group.

The “heterocyclic group” described herein is a ring group including atleast one hetero atom in the ring atom. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a siliconatom, a phosphorus atom and a boron atom.

The “heterocyclic group” described herein may be a monocyclic group, ora fused ring group.

The “heterocyclic group” described herein may be an aromaticheterocyclic group, or an aliphatic heterocyclic group.

Specific examples (specific example group G2) of the “substituted orunsubstituted heterocyclic group” include an unsubstituted heterocyclicgroup and a substituted heterocyclic group described below. (Here, theunsubstituted heterocyclic group refers to a case where the “substitutedor unsubstituted heterocyclic group” is the “unsubstituted heterocyclicgroup,” and the substituted heterocyclic group refers to a case wherethe “substituted or unsubstituted heterocyclic group” is the“substituted heterocyclic group”. Hereinafter, the case of merely“heterocyclic group” includes both the “unsubstituted heterocyclicgroup” and the “substituted heterocyclic group”.

The “substituted heterocyclic group” refers to a case where the“unsubstituted heterocyclic group” has a substituent, and specificexamples thereof include a group in which the “unsubstitutedheterocyclic group” has a substituent, and a substituted heterocyclicgroup described below. It should be noted that examples of the“unsubstituted heterocyclic group” and examples of the “substitutedheterocyclic group” listed herein are merely one example, and the“substituted heterocyclic group” described herein also includes a groupin which “unsubstituted heterocyclic group” which has a substituentfurther has a substituent, and a group in which “substitutedheterocyclic group” further has a substituent, and the like.

An unsubstituted heterocyclic group including a nitrogen atom:

a pyrrolyl group,an imidazolyl group,a pyrazolyl group,a triazolyl group,a tetrazolyl group,an oxazolyl group,an isoxazolyl group,an oxadiazolyl group,a thiazolyl group,an isothiazolyl group,a thiadiazolyl group,a pyridyl group,a pyridazinyl group,a pyrimidinyl group,a pyrazinyl group,a triazinyl group,an indolyl group,an isoindolyl group,an indolizinyl group,a quinolizinyl group,a quinolyl group,an isoquinolyl group,a cinnolyl group,a phthalazinyl group,a quinazolinyl group,a quinoxalinyl group,a benzimidazolyl group,an indazolyl group,a phenanthrolinyl group,a phenanthridinyl groupan acridinyl group,a phenazinyl group,a carbazolyl group,a benzocarbazolyl group,a morpholino group,a phenoxazinyl group,a phenothiazinyl group,an azacarbazolyl group, anda diazacarbazolyl group.

An unsubstituted heterocyclic group including an oxygen atom:

a furyl group,an oxazolyl group,an isoxazolyl group,an oxadiazolyl group,a xanthenyl group,a benzofuranyl group,an isobenzofuranyl group,a dibenzofuranyl group,a naphthobenzofuranyl group,a benzoxazolyl group,a benzisoxazolyl group,a phenoxazinyl group,a morpholino group,a dinaphthofuranyl group,an azadibenzofuranyl group,a diazadibenzofuranyl group,an azanaphthobenzofuranyl group, anda diazanaphthobenzofuranyl group.

An unsubstituted heterocyclic group including a sulfur atom:

a thienyl group,a thiazolyl group,an isothiazolyl group,a thiadiazolyl group,a benzothiophenyl group,an isobenzothiophenyl group,a dibenzothiophenyl group,a naphthobenzothiophenyl group,a benzothiazolyl group,a benzisothiazolyl group,a phenothiazinyl group,a dinaphthothiophenyl group,an azadibenzothiophenyl group,a diazadibenzothiophenyl group,an azanaphthobenzothiophenyl group, anda diazanaphthobenzothiophenyl group.

A substituted heterocyclic group including a nitrogen atom:

a (9-phenyl)carbazolyl group,a (9-biphenylyl)carbazolyl group,a (9-phenyl)phenylcarbazolyl group,a (9-naphthyl)carbazolyl group,a diphenylcarbazol-9-yl group,a phenylcarbazol-9-yl group,a methylbenzimidazolyl group,an ethylbenzimidazolyl group,a phenyltriazinyl group,a biphenylyltriazinyl group,a diphenyltriazinyl group,a phenylquinazolinyl group, anda biphenylylquinazolinyl group.A substituted heterocyclic group including an oxygen atom:a phenyldibenzofuranyl group,a methyldibenzofuranyl group,a t-butyldibenzofuranyl group, anda monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].

A substituted heterocyclic group including a sulfur atom:

a phenyldibenzothiophenyl group,a methyldibenzothiophenyl group,a t-butyldibenzothiophenyl group, anda monovalent residue of spiro[9H-thioxantene-9,9′-[9H]fluorene].

A monovalent group derived from the following unsubstituted heterocyclicring containing at least one of a nitrogen atom, an oxygen atom and asulfur atom by removal of one hydrogen atom bonded to the ring atomsthereof, and a monovalent group in which a monovalent group derived fromthe following unsubstituted heterocyclic ring has a substituent byremoval of one hydrogen atom bonded to the ring atoms thereof:

In the formulas (XY-1) to (XY-18), X_(A) and Y_(A) are independently anoxygen atom, a sulfur atom, NH or CH₂. However, at least one of X_(A)and Y_(A) is an oxygen atom, a sulfur atom or NH.

The heterocyclic ring represented by the formulas (XY-1) to (XY-18)becomes a monovalent heterocyclic group including a bond at an arbitraryposition.

An expression “the monovalent group derived from the unsubstitutedheterocyclic ring represented by the formulas (XY-1) to (XY-18) has asubstituent” refers to a case where the hydrogen atom bonded with thecarbon atom which constitutes a skeleton of the formulas is substitutedby a substituent, or a state in which X_(A) or Y_(A) is NH or CH₂, andthe hydrogen atom in the NH or CH₂ is replaced with a substituent.

Specific examples (specific example group G3) of the “substituted orunsubstituted alkyl group” include an unsubstituted alkyl group and asubstituted alkyl group described below. (Here, the unsubstituted alkylgroup refers to a case where the “substituted or unsubstituted alkylgroup” is the “unsubstituted alkyl group,” and the substituted alkylgroup refers to a case where the “substituted or unsubstituted alkylgroup” is the “substituted alkyl group”). Hereinafter, the case ofmerely “alkyl group” includes both the “unsubstituted alkyl group” andthe “substituted alkyl group”.

The “substituted alkyl group” refers to a case where the “unsubstitutedalkyl group” has a substituent, and specific examples thereof include agroup in which the “unsubstituted alkyl group” has a substituent, and asubstituted alkyl group described below. It should be noted thatexamples of the “unsubstituted alkyl group” and examples of the“substituted alkyl group” listed herein are merely one example, and the“substituted alkyl group” described herein also includes a group inwhich “unsubstituted alkyl group” has a substituent further has asubstituent, a group in which “substituted alkyl group” further has asubstituent, and the like.

An unsubstituted alkyl group:

a methyl group,an ethyl group,a n-propyl group,an isopropyl group,a n-butyl group,an isobutyl group,a s-butyl group, anda t-butyl group.

A substituted alkyl group:

a heptafluoropropyl group (including an isomer),a pentafluoroethyl group,a 2,2,2-trifluoroethyl group, anda trifluoromethyl group.

Specific examples (specific example group G4) of the “substituted orunsubstituted alkenyl group” include an unsubstituted alkenyl group anda substituted alkenyl group described below. (Here, the unsubstitutedalkenyl group refers to a case where the “substituted or unsubstitutedalkenyl group” is the “unsubstituted alkenyl group,” and the substitutedalkenyl group refers to a case where the “substituted or unsubstitutedalkenyl group” is the “substituted alkenyl group”). Hereinafter, thecase of merely “alkenyl group” includes both the “unsubstituted alkenylgroup” and the “substituted alkenyl group”.

The “substituted alkenyl group” refers to a case where the“unsubstituted alkenyl group” has a substituent, and specific examplesthereof include a group in which the “unsubstituted alkenyl group” has asubstituent, and a substituted alkenyl group described below. It shouldbe noted that examples of the “unsubstituted alkenyl group” and examplesof the “substituted alkenyl group” listed herein are merely one example,and the “substituted alkenyl group” described herein also includes agroup in which “unsubstituted alkenyl group” has a substituent furtherhas a substituent, a group in which “substituted alkenyl group” furtherhas a substituent, and the like.

An unsubstituted alkenyl group and a substituted alkenyl group:

a vinyl group,an allyl group,a 1-butenyl group,a 2-butenyl group,a 3-butenyl group,a 1,3-butanedienyl group,a 1-methylvinyl group,a 1-methylallyl group,a 1,1-dimethylallyl group,a 2-methylallyl group, anda 1,2-dimethylallyl group.

Specific examples (specific example group G5) of the “substituted orunsubstituted alkynyl group” include an unsubstituted alkynyl groupdescribed below. (Here, the unsubstituted alkynyl group refers to a casewhere the “substituted or unsubstituted alkynyl group” is the“unsubstituted alkynyl group”). Hereinafter, a case of merely “alkynylgroup” includes both the “unsubstituted alkynyl group” and the“substituted alkynyl group”.

The “substituted alkynyl group” refers to a case where the“unsubstituted alkynyl group” has a substituent, and specific examplesthereof include a group in which the “unsubstituted alkynyl group”described below has a substituent.

An unsubstituted alkynyl group:

an ethynyl group.

Specific examples (specific example group G6) of the “substituted orunsubstituted cycloalkyl group” described herein include anunsubstituted cycloalkyl group and a substituted cycloalkyl groupdescribed below. (Here, the unsubstituted cycloalkyl group refers to acase where the “substituted or unsubstituted cycloalkyl group” is the“unsubstituted cycloalkyl group,” and the substituted cycloalkyl grouprefers to a case where the “substituted or unsubstituted cycloalkylgroup” is the “substituted cycloalkyl group”). Hereinafter, a case ofmerely “cycloalkyl group” includes both the “unsubstituted cycloalkylgroup” and the “substituted cycloalkyl group”.

The “substituted cycloalkyl group” refers to a case where the“unsubstituted cycloalkyl group” a the substituent, and specificexamples thereof include a group in which the “unsubstituted cycloalkylgroup” has a substituent, and a substituted cycloalkyl group describedbelow. It should be noted that examples of the “unsubstituted cycloalkylgroup” and examples of the “substituted cycloalkyl group” listed hereinare merely one example, and the “substituted cycloalkyl group” describedherein also includes a group in which “unsubstituted cycloalkyl group”has a substituent further has a substituent, a group in which“substituted cycloalkyl group” further has a substituent, and the like.

An unsubstituted aliphatic ring group:

a cyclopropyl group,a cyclobutyl group,a cyclopentyl group,a cyclohexyl group,a 1-adamantyl group,a 2-adamantyl group,a 1-norbornyl group, anda 2-norbornyl group.

A substituted cycloalkyl group:

a 4-methylcyclohexyl group.

Specific examples (specific example group G7) of the group representedby

—Si(R901)(R902)(R903) described herein include

—Si(G1)(G1)(G1), —Si(G1)(G2)(G2), —Si(G1)(G1)(G2), —Si(G2)(G2)(G2),—Si(G3)(G3)(G3), —Si(G5)(G5)(G5) and —Si(G6)(G6)(G6).

In which,

G1 is the “aryl group” described in the specific example group G1.

G2 is the “heterocyclic group” described in the specific example groupG2.

G3 is the “alkyl group” described in the specific example group G3.

G5 is the “alkynyl group” described in the specific example group G5.

G6 is the “cycloalkyl group” described in the specific example group G6.

Specific examples (specific example group G8) of the group representedby —O—(R904) described herein include

—O(G1), —O(G2), —O(G3) and —O(G6).

In which,

G1 is the “aryl group” described in the specific example group G1.

G2 is the “heterocyclic group” described in the specific example groupG2.

G3 is the “alkyl group” described in the specific example group G3.

G6 is the “cycloalkyl group” described in the specific example group G6.

Specific examples (specific example group G9) of the group representedby —S—(R905) described herein include

—S(G1), —S(G2), —S(G3) and —S(G6).

In which,

G1 is the “aryl group” described in the specific example group G1.

G2 is the “heterocycle group” described in the specific example groupG2.

G3 is the “alkyl group” described in the specific example group G3.

G6 is the “cycloalkyl group” described in the specific example group G6.

Specific examples (specific example group G10) of the group representedby —N(R₉₀₆)(R₉₀₇) described herein include

—N(G1)(G1), —N(G2)(G2), —N(G1)(G2), —N(G3)(G3) and —N(G6) (G6).

In which,

G1 is the “aryl group” described in the specific example group G1.

G2 is the “heterocycle group” described in the specific example groupG2.

G3 is the “alkyl group” described in the specific example group G3.

G6 is the “cycloalkyl group” described in the specific example group G6.

Specific examples (specific example group G11) of the “halogen atom”described herein include a fluorine atom, a chlorine atom, a bromineatom and an iodine atom.

Specific examples of the “alkoxy group” described herein include a grouprepresented by —O(G3), where G3 is the “alkyl group” described in thespecific example group G3. The number of carbon atoms of the“unsubstituted alkoxy group” are 1 to 50, preferably 1 to 30, and morepreferably 1 to 18, unless otherwise specified.

Specific examples of the “alkylthio group” described herein include agroup represented by —S(G3), where G3 is the “alkyl group” described inthe specific example group G3. The number of carbon atoms of the“unsubstituted alkylthio group” are 1 to 50, preferably 1 to 30, andmore preferably 1 to 18, unless otherwise specified.

Specific examples of the “aryloxy group” described herein include agroup represented by —O(G1), where G1 is the “aryl group” described inthe specific example group G1. The number of ring carbon atoms of the“unsubstituted aryloxy group” are 6 to 50, preferably 6 to 30, and morepreferably 6 to 18, unless otherwise specified.

Specific examples of the “arylthio group” described herein include agroup represented by —S(G1), where G1 is the “aryl group” described inthe specific example group G1. The number of ring carbon atoms of the“unsubstituted arylthio group” are 6 to 50, preferably 6 to 30, and morepreferably 6 to 18, unless otherwise specified.

Specific examples of the “aralkyl group” described herein include agroup represented by -(G3)-(G1), where G3 is the “alkyl group” describedin the specific example group G3, and G1 is the “aryl group” describedin the specific example group G1. Accordingly, the “aralkyl group” isone embodiment of the “substituted alkyl group” substituted by the “arylgroup”. The number of carbon atoms of the “unsubstituted aralkyl group,”which is the “unsubstituted alkyl group” substituted by the“unsubstituted aryl group,” are 7 to 50, preferably 7 to 30, and morepreferably 7 to 18, unless otherwise specified.

Specific example of the “aralkyl group” include a benzyl group, a1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethylgroup, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, aβ-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethylgroup, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

The substituted or unsubstituted aryl group described herein is, unlessotherwise specified, preferably a phenyl group, a p-biphenyl group, am-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, ap-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-ylgroup, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, ano-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-ylgroup, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, aphenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenylgroup, a fluorenyl group, a 9,9′-spirobifluorenyl group, a9,9-diphenylfluorenyl group, or the like.

The substituted or unsubstituted heterocyclic group described herein is,unless otherwise specified, preferably a pyridyl group, a pyrimidinylgroup, a triazinyl group, a quinolyl group, an isoquinolyl group, aquinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, acarbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), abenzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group,a dibenzofuranyl group, a naphthobenzofuranyl group, anazadibenzofuranyl group, a diazadibenzofuranyl group, adibenzothiophenyl group, a naphthobenzothiophenyl group, anazadibenzothiophenyl group, a diazadibenzothiophenyl group, a(9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a(9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a(9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a(9-phenyl)phenylcarbazolyl group, a diphenylcarbazole-9-yl group, aphenylcarbazol-9-yl group, a phenyltriazinyl group, abiphenylyltriazinyl group, diphenyltriazinyl group, aphenyldibenzofuranyl group, a phenyldibenzothiophenyl group, anindrocarbazolyl group, a pyrazinyl group, a pyridazinyl group, aquinazolinyl group, a cinnolinyl group, a phthalazinyl group, aquinoxalinyl group, a pyrrolyl group, an indolyl group, apyrrolo[3,2,1-jk]carbazolyl group, a furanyl group, a benzofuranylgroup, a thiophenyl group, a benzothiophenyl group, a pyrazolyl group,an imidazolyl group, a benzimidazolyl group, a triazolyl group, anoxazolyl group, a benzoxazolyl group, a thiazolyl group, abenzothiazolyl group, an isothiazolyl group, a benzisothiazolyl group, athiadiazolyl group, an isoxazolyl group, a benzisoxazolyl group, apyrrolidinyl group, a piperidinyl group, a piperazinyl group, animidazolidinyl group, an indro[3,2,1-jk]carbazolyl group, adibenzothiophenyl group, or the like.

The dibenzofuranyl group and the dibenzothiophenyl group as describedabove are specifically any group described below, unless otherwisespecified.

In the formulas (XY-76) to (XY-79), XB is an oxygen atom or a sulfuratom.

The substituted or unsubstituted alkyl group described herein is, unlessotherwise specified, preferably a methyl group, an ethyl group, a propylgroup, an isopropyl group, a n-butyl group, an isobutyl group, a t-butylgroup, or the like.

The “substituted or unsubstituted arylene group” descried herein refersto a group in which the above-described “aryl group” is converted intodivalence, unless otherwise specified. Specific examples (specificexample group G12) of the “substituted or unsubstituted arylene group”include a group in which the “aryl group” described in the specificexample group G1 is converted into divalence. Namely, specific examples(specific example group G12) of the “substituted or unsubstitutedarylene group” refer to a group derived from the “aryl group” describedin specific example group G1 by removal of one hydrogen atom bonded tothe ring carbon atoms thereof.

Specific examples (specific example group G13) of the “substituted orunsubstituted divalent heterocyclic group” include a group in which the“heterocyclic group” described in the specific example group G2 isconverted into divalence. Namely, specific examples (specific examplegroup G13) of the “substituted or unsubstituted divalent heterocyclicgroup” refer to a group derived from the “heterocyclic group” describedin specific example group G2 by removal of one hydrogen atom bonded tothe ring atoms thereof.

Specific examples (specific example group G14) of the “substituted orunsubstituted alkylene group” include a group in which the “alkyl group”described in the specific example group G3 is converted into divalence.Namely, specific examples (specific example group G14) of the“substituted or unsubstituted alkylene group” refer to a group derivedfrom the “alkyl group” described in specific example group G3 by removalof one hydrogen atom bonded to the carbon atoms constituting the alkanestructure thereof.

The substituted or unsubstituted arylene group described herein is anygroup described below, unless otherwise specified.

In the formulas (XY-20) to (XY-29), (XY-83) and (XY-84), R₉₀₈ is asubstituent.

Then, m901 is an integer of 0 to 4, and when m901 is 2 or more, aplurality of R₉₀₈ may be the same with or different from each other.

In the formulas (XY-30) to (XY-40), R₉₀₉ is independently a hydrogenatom or a substituent. Two of R₉₀₉ may form a ring by bonding with eachother through a single bond.

In the formulas (XY-41) to (XY-46), R₉₁₀ is a substituent.

Then, m902 is an integer of 0 to 6. When m902 is 2 or more, a pluralityof R₉₁₀ may be the same with or different from each other.

The substituted or unsubstituted divalent heterocyclic group describedherein is preferably any group described below, unless otherwisespecified.

In the formulas (XY-50) to (XY-60), R₉₁₁ is a hydrogen atom or asubstituent.

In the formulas (XY-65) to (XY-75), X_(B) is an oxygen atom or a sulfuratom.

Herein, a case where “one or more sets of two or more groups adjacent toeach other form a substituted or unsubstituted and saturated orunsaturated ring by bonding with each other” will be described bytaking, as an example, a case of an anthracene compound represented bythe following formula (XY-80) in which a mother skeleton is ananthracene ring.

For example, two adjacent to each other into one set when “one or moresets of two or more groups adjacent to each other form the ring bybonding with each other” among R₉₂₁ to R₉₃₀ include R₉₂₁ and R₉₂₂, R₉₂₂and R₉₂₃, R₉₂₃ and R₉₂₄, R₉₂₄ and R₉₃₀, R₉₃₀ and R₉₂₅, R₉₂₅ and R₉₂₆,R₉₂₆ and R₉₂₇, R₉₂₇ and R₉₂₈, R₉₂₈ and R₉₂₉, and R₉₂₉ and R₉₂₁.

The above-described “one or more sets” means that two or more sets oftwo groups adjacent to each other may simultaneously form the ring. Forexample, a case where R₉₂₁ and R₉₂₂ forma ring A by bonding with eachother, and simultaneously R₉₂₅ and R₉₂₆ form a ring B by bonding witheach other is represented by the following formula (XY-81).

A case where “two or more groups adjacent to each other” form a ringmeans that, for example, R₉₂₁ and R₉₂₂ form a ring A by bonding witheach other, and R₉₂₂ and R₉₂₃ form a ring C by bonding with each other.A case where the ring A and ring C sharing R₉₂₂ are formed, in which thering A and the ring Care fused to the anthracene mother skeleton bythree of R₉₂₁ to R₉₂₃ adjacent to each other, is represented by thefollowing (XY-82).

The rings A to C formed in the formulas (XY-81) and (XY-82) are asaturated or unsaturated ring.

A term “unsaturated ring” means an aromatic hydrocarbon ring or anaromatic heterocyclic ring. A term “saturated ring” means an aliphatichydrocarbon ring or an aliphatic heterocyclic ring.

For example, the ring A formed by R₉₂₁ and R₉₂₂ being bonded with eachother, represented by the formula (XY-81), means a ring formed by acarbon atom of the anthracene skeleton bonded with R₉₂₁, a carbon atomof the anthracene skeleton bonded with R₉₂₂, and one or more arbitraryelements. Specific examples include, when the ring A is formed by R₉₂₁and R₉₂₂, a case where an unsaturated ring is formed of a carbon atom ofan anthracene skeleton bonded with R₉₂₁, a carbon atom of the anthraceneskeleton bonded with R₉₂₂, and four carbon atoms, in which a ring formedby R₉₂₁ and R₉₂₂ is formed into a benzene ring. Further, when asaturated ring is formed, the ring is formed into a cyclohexane ring.

Here, “arbitrary elements” are preferably a C element, a N element, an Oelement and a S element. In the arbitrary elements (for example, a caseof the C element or the N element), the bond(s) that is(are) notinvolved in the formation of the ring may be terminated by a hydrogenatom, or may be substituted by an arbitrary substituent. When the ringcontains the arbitrary elements other than the C element, the ring to beformed is a heterocyclic ring.

The number of “one or more arbitrary elements” forming the saturated orunsaturated ring is preferably 2 or more and 15 or less, more preferably3 or more and 12 or less, and further preferably 3 or more and 5 orless.

As specific examples of the aromatic hydrocarbon ring, a structure inwhich the aryl group described in specific example group G1 isterminated with a hydrogen atom may be mentioned.

As specific examples of the aromatic heterocyclic ring, a structure inwhich the aromatic heterocyclic group described in specific examplegroup G2 is terminated with a hydrogen atom may be mentioned.

As specific examples of the aliphatic hydrocarbon ring, a structure inwhich the cycloalkyl group described in specific example group G6 isterminated with a hydrogen atom may be mentioned.

When the above-described “saturated or unsaturated ring” has asubstituent, the substituent is an “arbitrary substituent” as describedbelow, for example. When the above-mentioned “saturated or unsaturatedring” has a substituent, specific examples of the substituent refer tothe substituents described in above-mentioned “the substituent describedherein”.

In one embodiment of this specification, the substituent (hereinafter,referred to as an “arbitrary substituent” in several cases) in the caseof the “substituted or unsubstituted” is a group selected from the groupconsisting of

an unsubstituted alkyl group including 1 to 50 carbon atoms,an unsubstituted alkenyl group including 2 to 50 carbon atoms,an unsubstituted alkynyl group including 2 to 50 carbon atoms,an unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅)

—N(R₉₀₆)(R₉₀₇)wherein,R₉₀₁ to R₉₀₇ are independentlya hydrogen atom,a substituted or unsubstituted alkyl group including 1 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group including 3 to 50 ringcarbon atoms,a substituted or unsubstituted aryl group including 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group including 5to 50 ring atoms; and when two or more of R₉₀₁ to R₉₀₇ exist, two ormore of R₉₀₁ to R₉₀₇ may be the same with or different from each other,a halogen atom, a cyano group, a nitro group,an unsubstituted aryl group including 6 to 50 ring carbon atoms, andan unsubstituted monovalent heterocyclic group including 5 to 50 ringatoms.

In one embodiment, the substituent in the case of “substituted orunsubstituted” is a group selected from the group consisting of

an alkyl group including 1 to 50 carbon atoms,an aryl group including 6 to 50 ring carbon atoms, anda monovalent heterocyclic group including 5 to 50 ring atoms.

In one embodiment, the substituent in the case of “substituted orunsubstituted” is a group selected from the group consisting of

an alkyl group including 1 to 18 carbon atoms,an aryl group including 6 to 18 ring carbon atoms, anda monovalent heterocyclic group including 5 to 18 ring atoms.

Specific examples of each group of the arbitrary substituent describedabove are as described above.

Herein, unless otherwise specified, the saturated or unsaturated ring(preferably substituted or unsubstituted and saturated or unsaturatedfive-membered or six-membered ring, more preferably a benzene ring) maybe formed by the arbitrary substituents adjacent to each other.

Herein, unless otherwise specified, the arbitrary substituent mayfurther have the substituent. Specific examples of the substituent thatthe arbitrary substituent further has include to the ones same as thearbitrary substituent described above.

[New Compound]

The compound according to one aspect of the invention is represented bythe following formula (1) or (2).

In the formulas (1) and (2),

R₁ to R₈ and R₁₁ to R₁₄ are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

R₁₅ to R₁₈ are hydrogen atoms;

R₉₀₁ to R₉₀₇ are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

when two or more of R₉₀₁ to R₉₀₇ exist, two or more of R₉₀₁ to R₉₀₇ maybe the same with or different from each other;

at least one of R₁ to R₈ is a deuterium atom;

two or more adjacent groups of R₁ to R₄, two or more adjacent groups ofR₅ to R₈ and two or more adjacent groups of R₁₁ to R₁₄ do not form aring;

L₁ and L₂ are independently

a single bond,a substituted or unsubstituted arylene group having 6 to 30 ring carbonatoms, ora substituted or unsubstituted divalent heterocyclic group having 5 to30 ring atoms;

Ar is

a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms.

By having the above structure, the compound according to one aspect ofthe invention can enhance the device performance when the compound isused in an organic EL device. Specifically, it is possible to provide anorganic EL device with longer life.

According to one aspect of the present invention, a method for improvinga performance of an organic EL device can also be provided. the methodis characterized in that the above compound is used in the emittinglayer of the organic EL device. Specifically, the method can improve anorganic EL device performance as compared with the case where a compoundhaving the same structure as formula (1) or (2) except that only protiumatoms are contained as hydrogen atoms (hereinafter also referred to as“protium compound”) is used as a host material. The case where theprotium compound is used means that a host material in an emitting layerconsists essentially of the protium compound (the ratio of the protiumcompound to the sum of the protium compound and the compound representedby formula (1) or (2) is 90 mol % or more, 95 mol % or more, or 99 mol %or more).

That is, it is possible to increase a performance of an organic ELdevice by, instead of a protium compound or in addition to a protiumcompound, using a compound obtained by replacing at least one protiumatoms on an anthracene skeleton of the protium compound with a deuteriumatom (a compound represented by formula (1) or (2)) as a host material.

All of R₁ to R₈ may be deuterium atoms or a part of them (e.g., one ortwo or more of R₁ to R₈) may be deuterium atoms.

R₁ to R₈ that are not deuterium atoms are preferably hydrogen atoms(protium atoms).

In one embodiment, at least one hydrogen atom contained in one or moregroups selected from a group consisting of L₁ and L₂ is a deuteriumatom. In more detail, in one embodiment, one or more groups selectedfrom the group consisting of L₁ and L₂ are an unsubstituted arylenegroup having 6 to 30 ring carbon atoms in which at least one hydrogenatom is a deuterium atom, or an unsubstituted divalent heterocyclicgroup having 5 to 30 ring atoms in which at least one hydrogen atom is adeuterium atom.

In one embodiment, L₁ and L 2 are independently a single bond, or asubstituted or unsubstituted arylene group having 6 to 14 ring carbonatoms. It is preferable that at least one of L₁ and L₂ is a single bond.

In one embodiment, R₁₁ to R₁₄ are hydrogen atoms.

In one embodiment, at least one R₁₁ to R₁₈ is a deuterium atom.

In one embodiment, at least one hydrogen atom contained in one or moreAr is a deuterium atom. In more detail, in one embodiment, Ar is anunsubstituted aryl group having 6 to 50 ring carbon atoms in which atleast one hydrogen atom is a deuterium atom, or an unsubstitutedmonovalent heterocyclic group having 5 to 50 ring atoms in which atleast one hydrogen atom is a deuterium atom.

Ar is preferably a substituted or unsubstituted aryl group having 6 to50 ring carbon atoms, more preferably selected from groups representedby the following formulas (a1) to (a4).

In the formulas (a1) to (a4), * is a single bond bonding to L₁;

R₂₁ is independently

a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

R₉₀₁ to R₉₀₇ are as defined in the formula (1);

m1 is independently an integer of 0 to 4;

m2 is independently an integer of 0 to 5;

m3 is independently an integer of 0 to 7;

when each of m1 to m3 is 2 or more, the plural R₂₁s may be the same ordifferent; and

when each of m1 to m3 is 2 or more, adjacent plural R₂₁s are bonded witheach other to form a substituted or unsubstituted, saturated orunsaturated ring, or do not form a substituted or unsubstituted,saturated or unsaturated ring.

A bond position on L₂ side on the dibenzofuran skeleton, that is, atpositions 1, 3, and 4 of dibenzofuran in formula (1), and at positions2, 3, and 4 of dibenzofuran in formula (2), all of which are bonded tohydrogen atom, may be deuterium atom, or may be one or more (forexample, positions 1 and 4 in formula (1), and positions 2 and 4 informula (2)).

Existence of a deuterium atom in the compound is confirmed by MassSpectrometry or ¹H-NMR Spectrometry. The bonding position of a deuteriumatom in the compound is identified by ¹H-NMR Spectrometry. In concreteterms, it is confirmed as follows.

If it is identified that, by Mass Spectrometry, a molecular weight of atarget compound is greater by “one” than a molecular weight of acorresponding compound in which all hydrogen atoms are protium atoms, itis confirmed that one deuterium atom exists in the target compound.Further, the number of deuterium atoms in a molecule can be confirmed byan integration value obtained by ¹H-NMR analysis on the target compound,since no signal is observed by performing ¹H-NMR analysis on a deuteriumatom. The bonding position of a deuterium can be identified byperforming ¹H-NMR analysis on the target compound and assigning signals.

The composition according to one aspect of the invention contains thecompound represented by formula (1) or (2), and the content ratio of theprotium compound to the total of the compound represented by formula (1)or (2) and the protium compound is preferably 99 mol % or less. Thecontent ratio of the protium compound is confirmed by Mass Spectrometry.

In the composition according to one aspect of the invention, the contentratio of the compound represented by formula (1) or (2) to the total ofthe compound represented by formula (1) or (2) and the protium compoundis 30 mol % or more, 50 mol % or more, 70 mol % or more, 90 mol % ormore, 95 mol % or more, 99 mol % or more, or 100 mol %.

In one embodiment, the compound represented by the formula (1) is acompound represented by following formula (1-1) and the compoundrepresented by the formula (2) is a compound represented by followingformula (2-1).

In the formulas (1-1) and (2-1), R₁ to R₃, Ar, L₁ and L₂ are as definedin the formula (1).

In one embodiment, the compound represented by the formula (1) is acompound represented by following formula (1-2) and the compoundrepresented by the formula (2) is a compound represented by followingformula (2-2).

In the formulas (1-2) and (2-2), Ar, L₁ and L₂ are as defined in theformula (1).

The compound represented by the formula (1) or (2) can be synthesized inaccordance with the synthesis process described in Examples by usingpublicly known alternative reactions or materials corresponding to atarget compound.

Examples of the compound according to one aspect of the inventioninclude the following compounds. In the specific examples, D representsdeuterium atom.

The above compound can be used as a material for organic EL device,preferably a host material for an emitting layer.

[Organic EL Device]

The organic EL device according to one aspect of the invention comprisesa cathode, an anode and one or two or more organic layer disposedbetween the cathode and the anode, and at least one organic layercomprises the compound represented by formula (1) or (2), or thecomposition of the invention described above. A conventionally knownmaterial, device configuration can be applied, except that at least oneof organic layer comprises the compound represented by formula (1) or(2), or the composition of the invention described above, as long as theadvantageous effect of the Invention is not impaired. In the aboveorganic EL device, one or two or more organic layers preferably compriseemitting layer and the emitting layer comprises the compound representedby formula (1) or (2), or the composition of the invention describedabove.

In one embodiment, the emitting layer of the organic EL device accordingto one aspect of the invention contains the compound represented byformula (1) or (2) and the protium compound, and the content ratio ofthe protium compound to the total of the compound represented by formula(1) or (2) and the protium compound is 99 mol % or less.

In one embodiment, the emitting layer of the organic EL device accordingto one aspect of the invention contains the compound represented byformula (1) or (2) and the protium compound, and the content ratio ofthe compound represented by formula (1) or (2) to the total of thecompound represented by formula (1) or (2) and the protium compound is30 mol % or more, 50 mol % or more, 70 mol % or more, 90 mol % or more,95 mol % or more, 99 mol % or more, or 100 mol %.

One embodiment of the organic EL device preferably has thehole-transporting layer between the anode and the emitting layer.

One embodiment of the organic EL device preferably has theelectron-transporting layer between the cathode and the emitting layer.

Specific examples of a typified device configuration of the organic ELdevice of the invention include structures such as

(1) an anode/an emitting layer/a cathode,(2) an anode/a hole-injecting layer/an emitting layer/a cathode,(3) an anode/an emitting layer/an electron-injecting-transportinglayer/a cathode,(4) an anode/a hole-injecting layer/an emitting layer/anelectron-injecting-transporting layer/a cathode,(5) an anode/an organic semiconductor layer/an emitting layer/a cathode,(6) an anode/an organic semiconductor layer/an electron barrier layer/anemitting layer/a cathode,(7) an anode/an organic semiconductor layer/an emitting layer/anadhesion improving layer/a cathode,(8) an anode/a hole-injecting-transporting layer/an emitting layer/anelectron-injecting-transporting layer/a cathode,(9) an anode/an insulating layer/an emitting layer/an insulating layer/acathode,(10) an anode/an inorganic semiconductor layer/an insulating layer/anemitting layer/an insulating layer/a cathode,(11) an anode/an organic semiconductor layer/an insulating layer/anemitting layer/an insulating layer/a cathode,(12) an anode/an insulating layer/a hole-injecting-transporting layer/anemitting layer/an insulating layer/a cathode, and(13) an anode/an insulating layer/a hole-injecting-transporting layer/anemitting layer/an electron-injecting-transporting layer/a cathode.

Among the above-described structures, a configuration of (8) ispreferably used, but the configuration is not limited thereto.

In this specification, the term “hole-injecting-transporting layer”herein means “at least one of the hole-injecting layer and thehole-transporting layer”, and the term “electron-injecting-transportinglayer” herein means “at least one of the electron-injecting layer andthe electron-transporting layer”.

The emitting layer preferably comprises one or more compounds (dopantmaterial) selected from the group consisting of compounds represented bythe following formulas (11), (21), (31), (41), (51), (61), (71) and (81)in addition to the compound (host material) represented by the formula(1) or (2).

(Compound Represented by Formula (11))

The compound represented by the formula (11) is explained below.

In the formula (11),

one or more pairs of two or more adjacent groups of R₁₀₁ to R₁₁₀ arebonded with each other to form a substituted or unsubstituted, saturatedor unsaturated ring, or do not form a substituted or unsubstituted,saturated or unsaturated ring;

at least one of R₁₀₁ to R₁₁₀ is a monovalent group represented by theformula (12);

R₁₀₁ to R₁₁₁ that do not form the substituted or unsubstituted,saturated or unsaturated ring and that are not a monovalent grouprepresented by the following formula (12) are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

R₉₀₁ to R₉₀₇ are as defined in the formula (1);

wherein, in the formula (12), Ar₁₀₁ and Ar₁₀₂ are independently asubstituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or a substituted or unsubstituted monovalent heterocyclic grouphaving 5 to 50 ring atoms;

L₁₀₁ to L₁₀₃ are independently

a single bond,a substituted or unsubstituted arylene group having 6 to 30 ring carbonatoms, ora substituted or unsubstituted divalent heterocyclic group having 5 to30 ring atoms.

In the formula (11), it is preferable that two of R₁₀₁ to R₁₁₀ are thegroup represented by the formula (12).

In one embodiment, the compound represented by the formula (11) isrepresented by the following formula (13).

In the formula (13), R₁₁₁ to R₁₁₈ are the same as R₁₀₁ to R₁₁₀ that isnot a monovalent group represented by the formula (12) in the formula(11). Ar₁₀₁, Ar₁₀₂, L₁₀₁, L₁₀₂ and L₁₀₃ are as defined in the formula(12).

In the formula (11), L₁₀₁ is preferably a single bond and L₁₀₂ and L₁₀₃are preferably a single bond.

In one embodiment, the compound represented by the formula (11) isrepresented by the formula (14) or (15).

In the formula (14), R₁₁₁ to R₁₁₈ are as defined in the formula (13).Ar₁₀₁, Ar₁₀₂, L₁₀₂ and L₁₀₃ are as defined in the formula (12).

In the formula (15), R₁₁₁ to R₁₁₈ are as defined in the formula (13).Ar₁₀₁ and Ar₁₀₂ are as defined in the formula (12).

In the formula (11) and formula (12), it is preferable that at least oneof Ar₁₀₁ and Ar₁₀₂ is the group represented by the following formula(16).

In the formula (16),

X₁₀₁ is an oxygen atom or a sulfur atom;

one or more pairs of two or more adjacent groups of R₁₂₁ to R₁₂₇ arebonded with each other to form a substituted or unsubstituted, saturatedor unsaturated ring, or do not form a substituted or unsubstituted,saturated or unsaturated ring:

R₁₂₁ to R₁₂₇ that do not form the substituted or unsubstituted,saturated or unsaturated ring are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

R₉₀₁ to R₉₀₇ are as defined in the formula (1).

It is preferable that X₁₀₁ is an oxygen atom.

It is preferable that at least one of R₁₂₁ to R₁₂₇ is

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms.

It is preferable that in the formula (11) and formula (12), Ar₁₀₁ is agroup represented by the formula (16) and Ar₁₀₂ is a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the formula (11) isrepresented by the following formula (17).

In the formula (17), R₁₁₁ to R₁₁₈ are as defined in the formula (13),and R₁₂₁ to R₁₂₇ are as defined in the formula (16);

R₁₃₁ to R₁₃₅ are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; andR₉₀₁ to R₉₀₇ are as defined in the formula (1).

As the compound represented by the formula (11), the following compoundscan be given as specific examples, for example. In the following examplecompounds, Me represents methyl group.

(Compound Represented by Formula (21))

The compound represented by the formula (21) is explained below.

In the formula (21),

Zs are independently CR_(a) or N;

A1 ring and A2 ring are independently a substituted or unsubstitutedaromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or asubstituted or unsubstituted heterocyclic ring having 5 to 50 ringatoms;

when plural R_(a)s exist, one or more pairs of two or more adjacentgroups of R_(a) are bonded with each other to form a substituted orunsubstituted, saturated or unsaturated ring, or do not form asubstituted or unsubstituted, saturated or unsaturated ring;

when plural R_(b)s exist, one or more pairs of two or more adjacentgroups of R_(b) are bonded with each other to form a substituted orunsubstituted, saturated or unsaturated ring, or do not form asubstituted or unsubstituted, saturated or unsaturated ring;

when plural R_(c)s exist, one or more pairs of two or more adjacentgroups of R_(c) are bonded with each other to form a substituted orunsubstituted, saturated or unsaturated ring, or do not form asubstituted or unsubstituted, saturated or unsaturated ring;

n21 and n22 are independently an integer of 0 to 4;

R_(a) to R_(c) that do not form the substituted or unsubstituted,saturated or unsaturated ring are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;R₉₀₁ to R₉₀₇ are as defined in the formula (1).

The “aromatic hydrocarbon ring” of A1 ring and A2 ring has the samestructure as the compound obtained by introducing a hydrogen atom intothe “aryl group” described above.

The “aromatic hydrocarbon ring” of the A1 ring and the A2 ring containstwo carbon atoms in the fused bicyclic structure at the center of theformula (21) as ring atoms. Examples of “substituted or unsubstitutedaromatic hydrocarbon ring having 6 to 50 ring carbon atoms” includecompounds in which a hydrogen atom is introduced into the “aryl group”described in the example group G1.

The “heterocyclic ring” of A1 ring and A2 ring has the same structure asthe compound obtained by introducing a hydrogen atom into the“heterocyclic group” described above. The “heterocyclic ring” of the A1ring and the A2 ring contains two carbon atoms in the fused bicyclicstructure at the center of the formula (21) as ring atoms. Examples of“substituted or unsubstituted heterocyclic ring having 5 to 50 ringatoms” include compounds in which a hydrogen atom is introduced into the“heterocyclic group” described in the example group G2.

R_(b) is bonded to one of carbon atoms which form the aromatichydrocarbon ring of A1 ring, or one of atoms which form the heterocycleof A1 ring.

R_(c) is bonded to one of carbon atoms which form the aromatichydrocarbon ring of A2 ring, or one of atoms which form the heterocycleof A2 ring.

It is preferable that at least one (preferably two) of R_(a) to R_(c) isa group represented by the following formula (21a).

-L₂₀₁-Ar₂₀₁  (21a)

In the formula (21a),

L₂₀₁ is

a single bond,a substituted or unsubstituted arylene group having 6 to 30 ring carbonatoms, ora substituted or unsubstituted bivalent heterocyclic group having 5 to30 ring atoms;

Ar₂₀₁ is

a substituted or unsubstituted arylene group having 6 to 50 ring carbonatoms,a substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms, ora group represented by the following formula (21b):

wherein in the formula (21b),

L₂₁₁ and L₂₁₂ are independently

a single bond,a substituted or unsubstituted arylene group having 6 to 30 ring carbonatoms, ora substituted or unsubstituted divalent heterocyclic group having 5 to30 ring atoms;

Ar₂₁₁ and Ar₂₁₂ are bonded with each other to form a substituted orunsubstituted, saturated or unsaturated ring, or do not form asubstituted or unsubstituted, saturated or unsaturated ring; and

Ar₂₁₁ and Ar₂₁₂ that do not form a substituted or unsubstituted,saturated or unsaturated ring are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms or

a substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms.

In one embodiment, the compound represented by the formula (21) isrepresented by the following formula (22).

In the formula (22),

one or more pairs of two or more adjacent groups of R₂₀₁ to R₂₁₁ arebonded with each other to form a substituted or unsubstituted, saturatedor unsaturated ring, or do not form a substituted or unsubstitutedsaturated or unsaturated ring;

R₂₀₁ to R₂₁₁ that do not form the substituted or unsubstituted,saturated or unsaturated ring are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

R₉₀₁ to R₉₀₇ are as defined in the formula (1).

It is preferable that at least one (preferably two) of R₂₀₁ to R₂₁₁ isthe group represented by the formula (21a). It is preferable that R₂₀₄and R₂₁₁ are the group represented by the formula (21a).

In one embodiment, the compound represented by the formula (21) is acompound obtained by bonding the structure represented by the followingformula (21-1) or (21-2) to A1 ring. In one embodiment, the compoundrepresented by the formula (22) is a compound obtained by bonding thestructure represented by the following formula (21-1) or (21-2) to thering to which R₂₀₄ to R₂₀₇ bonds to.

In the formula (21-1), two bonds shown by * independently bond to a ringcarbon atom in the aromatic hydrocarbon ring or a ring atom in theheterocyclic group in A1 ring in the formula (21), or bond to one ofR₂₀₄ to R₂₀₇ in the formula (22);

wherein in the formula (21-2), three bonds shown by * independently bondto a ring carbon atom in the aromatic hydrocarbon ring or a ring atom inthe heterocyclic group in A1 ring in the formula (21), or bond to one ofR₂₀₄ to R₂₀₇ in the formula (22);

One or more pairs of two or more adjacent groups of R₂₂₁ to R₂₂₇ andR₂₃₁ to R₂₃₉ are bonded with each other to form a substituted orunsubstituted, saturated or unsaturated ring, or do not form asubstituted or unsubstituted, saturated or unsaturated ring;

R₂₂₁ to R₂₂₇ and R₂₃₁ to R₂₃₉ that do not form the substituted orunsubstituted, saturated or unsaturated ring are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

R₉₀₁ to R₉₀₇ are as defined in the formula (1).

In one embodiment, the compound represented by the formula (21) is acompound represented by the following formula (21-3), (21-4), or (21-5).

In the formulas (21-3), (21-4) and (21-5),

A1 ring is as defined in the formula (21);

R₂₄₀₁ to R₂₄₀₇ are the same as R₂₂₁ to R₂₂₇ in the formulas (21-1) and(21-2);

R₂₄₁₀ to R₂₄₁₇ are the same as R₂₀₁ to R₂₁₁ in the formula (22); and

two R₂₄₁₇ may be the same with or different from each other.

In one embodiment, the substituted or unsubstituted aromatic hydrocarbonring having 6 to 50 ring carbon atoms of A1 ring in the formula (21-5)is a substituted or unsubstituted napthalene ring, or a substituted orunsubstituted fluorene ring.

In one embodiment, the substituted or unsubstituted heterocycle having 5to 50 ring atoms of A1 ring in the formula (21-5) is a substituted orunsubstituted dibenzofuran ring, a substituted or unsubstitutedcarbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

In one embodiment, the compound represented by the formula (21) or (22)is selected from the group consisting of the compounds represented bythe following formulas (21-6-1) to (21-6-7).

In the formulas (21-6-1) to (21-6-7),

R₂₄₂₁ to R₂₄₂₇ are the same as R₂₂₁ to R₂₂₇ in the formulas (21-1) and(21-2);

R₂₄₃₀ to R₂₄₃₇ and R₂₄₄₁ to R₂₄₄₄ are the same as R₂₀₁ to R₂₁₁ in theformula (22);

X is O, NR901, or C(R₉₀₂) (R₉₀₃); and

R₉₀₁ to R₉₀₃ are as defined in the formula (1).

In one embodiment, in the compound represented by the formula (22), oneor more pairs of two or more adjacent groups of R₂₀₁ to R₂₁₁ are bondedwith each other to form a substituted or unsubstituted, saturated orunsaturated ring. This embodiment is described in the following formula(25).

(Compound Represented by Formula (25))

The compound represented by the formula (25) is explained below.

In the formula (25),

two or more pairs selected from a group consisting of R₂₅₁ and R₂₅₂,R₂₅₂ and R₂₅₃, R₂₅₄ and R₂₅₅, R₂₅₅ and R₂₅₆, R₂₅₆ and R₂₅₇, R₂₅₈ andR₂₅₉, R₂₅₉ and R₂₆₀, and R₂₆₀ and R₂₆₁ bond with each other to form asubstituted or unsubstituted, saturated or unsaturated ring;

Provided that the pair of R₂₅₁ and R₂₅₂ and the pair of R₂₅₂ and R₂₅₃ donot form a ring simultaneously; the pair of R₂₅₄ and R₂₅₅ and the pairof R₂₅₅ and R₂₅₆ do not form a ring simultaneously; the pair of R₂₅₅ andR₂₅₆ and the pair of R₂₅₆ and R₂₅₇ do not form a ring simultaneously;the pair of R₂₅₈ and R₂₅₉ and the pair of R₂₅₉ and R₂₆₀ do not form aring simultaneously; and the pair of R₂₅₉ and R₂₆₀ and the pair of R₂₆₀and R₂₆₁ do not form a ring simultaneously;

When two or more rings are formed by R₂₅₁ to R₂₆₁, the rings may be thesame or different;

R₂₅₁ to R₂₆₁ that do not form the substituted or unsubstituted,saturated or unsaturated ring are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms, or—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

R₉₀₁ to R₉₀₇ are as defined in the formula (1).

In the formula (25), R_(n) and R_(n+1) (n is an integer selected from251, 252, 254 to 256 and 258 to 260) bond with each other to form asubstituted or unsubstituted, saturated or unsaturated ring togetherwith two ring carbon atoms to which R_(n) and R_(n+1) bond with. Thering is preferably configured with atoms selected from C atom, O atom, Satom and N atom, and the number of atoms is preferably 3 to 7, morepreferably 5 or 6.

The number of the above-described ring structures in the compoundrepresented by the formula (25) is, for example, 2, 3 or 4. Two or morering structures may exist in the same benzene ring of the main skeletonin the formula (25), or may exist in different benzene rings. Forexample, the compound has three ring structures, one ring structure mayexist in each of the three benzene rings in the formula (25).

As the above-mentioned ring structure in the compound represented by theformula (25), structures represented by the following formulas (251) to(260) can be given, for example.

In the formulas (251) to (257),

each of *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and*12, and * 13 and * 14 represents two ring carbon atoms to which R_(n)and R_(n+1) bond, and R_(n) may bond to either one of the two ringcarbon atoms of *1 and * 2, * 3 and * 4, * 5 and * 6, * 7 and * 8, *9and *10, *11 and *12, and *13 and *14;

X2501 is C(R₂₅₁₂) (R₂₅₁₃), NR₂₅₁₄, O or S;

One or more pairs of two or more adjacent groups of R₂₅₀₁ to R₂₅₀₆ andR₂₅₁₂ to R₂₅₁₃ are bonded with each other to form a substituted orunsubstituted, saturated or unsaturated ring, or do not form asubstituted or unsubstituted saturated or unsaturated ring; and

R₂₅₀₁ to R₂₅₁₄ that do not form a substituted or unsubstituted saturatedor unsaturated ring are the same as R₂₅₁ to R₂₆₁.

In the formulas (258) to (260),

each of * 1 and * 2, and * 3 and * 4 represents two ring carbon atoms towhich R_(n) and R_(n+1) bond, and R_(n) may bond to either one of thetwo ring carbon atoms of * 1 and * 2, or * 3 and * 4;

X₂₅₀₁ is C(R₂₅₁₂) (R₂₅₁₃), NR₂₅₁₄, O or S;

One or more pairs of two or more adjacent groups of R₂₅₁₅ to R₂₅₂₅ bondto each other to form a substituted or unsubstituted, saturated orunsaturated ring, or do not form a substituted or unsubstitutedsaturated or unsaturated ring; and

R₂₅₁₅ to R₂₅₂₁ and R₂₅₂₂ to R₂₅₂₅ that do not form a substituted orunsubstituted saturated or unsaturated ring are the same as R₂₅₁ toR₂₆₁.

In the formula (25), it is preferable that at least one of R₂₅₂, R₂₅₄,R₂₅₅, R₂₆₀ and R₂₆₁ (preferably at least one of R₂₅₂, R₂₅₅, and R₂₆₀,more preferably R₂₅₂) is a group which does not form a ring.

-   (i) Substituent in the case where the ring structure formed by R_(n)    and R_(n)+1 has a substituent in the formula (25),-   (ii) R₂₅₁ to R₂₆₁ that do not form a ring structure in the formula    (25), and-   (iii) R₂Sol to R₂₅₁₄ and R₂₅₁₅ to R₂₅₂₅ in the formulas (251)    to (260) are preferably independently    a hydrogen atom,    a substituted or unsubstituted alkyl group having 1 to 50 carbon    atoms,    a substituted or unsubstituted alkenyl group having 2 to 50 carbon    atoms,    a substituted or unsubstituted alkynyl group having 2 to 50 carbon    atoms,    a substituted or unsubstituted cycloalkyl group having 3 to 50 ring    carbon atoms,    —N(R₉₀₆)(R₉₀₇),    a substituted or unsubstituted aryl group having 6 to 50 ring carbon    atoms,    a substituted or unsubstituted monovalent heterocyclic group having    5 to 50 ring atoms, or    a group selected from the following groups.

In the formulas (261) to (264),

R_(d)s are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

X is C(R₉₀₁)(R₉₀₂), NR₉₀₃, O, or S;

R₉₀₁ to R₉₀₇ are as defined in the formula (1); and

p1 is independently an integer of 0 to 5, p2 is independently an integerof 0 to 4, p3 is an integer of 0 to 3, and p4 is an integer of 0 to 7.

In one embodiment, the compound represented by the formula (25) isrepresented by the following formulas (25-1) to (25-6).

In the formulas (25-1) to (25-6), ring d to ring i are independently asubstituted or unsubstituted, saturated or unsaturated ring; and R₂₅₁ toR₂₆₁ are the same as defined in the formula (25).

In one embodiment, the compound represented by the formula (25) isrepresented by the following formulas (25-7) to (25-12).

In the formulas (25-7) to (25-12), ring d to ring f, ring k, and ring jare independently a substituted or unsubstituted, saturated orunsaturated ring; and R₂₅₁ to R₂₆₁ are the same as defined in theformula (25).

In one embodiment, the compound represented by the formula (25) isrepresented by the following formulas (25-13) to (25-21).

In the formulas (25-13) to (25-21), ring d to ring k are independently asubstituted or unsubstituted, saturated or unsaturated ring; and R₂₅₁ toR₂₆₁ are the same as defined in the formula (25).

As a substituent in the case where the ring g or ring h further has asubstituent, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted aryl group having 6 to 50ring carbon atoms, or a group represented by the formula (261), (263) or(264) can be given for example.

In one embodiment, the compound represented by the formula (25) isrepresented by one of the following formulas (25-22) to (25-25).

In the formulas (25-22) to (25-25), X250 is independently C(R₉₀₁)(R₉₀₂),NR₉₀₃, O or S; R₂₅₁ to R₂₆₁, and R₂₇₁ to R₂₇₈ are the same as R₂₅₁ toR₂₈₁ in the formula (25); and R₉₀₁ to R₉₀₃ are as defined in the formula(1).

In one embodiment, the compound represented by the formula (25) isrepresented by the following formula (25-26).

In the formula (25-26), X250 is C(R₉₀₁)(R₉₀₂), NR₉₀₃, O or S; R₂₅₃,R₂₅₄, R₂₅₇, R₂₅₈, R₂₆₁, and R₂₇₁ to R₂₈₂ are the same as R₂₅₁ to R₂₆₁ inthe formula (25); and R₉₀₁ to R₉₀₃ are as defined in the formula (1).

As the compound represented by the formula (21), the following compoundscan be shown for example. In the following example compounds, Merepresents methyl group.

(Compound Represented by Formula (31))

The compound represented by the formula (31) is explained below.

The compound represented by formula (31) is a compound corresponding tothe compound represented by the formula (21-3).

In the formula (31),

one or more pairs of two or more adjacent groups of R₃₀ to R₃₀₇ and R₃₁₁to R₃₁₇ form a substituted or unsubstituted, saturated or unsaturatedring, or do not form a substituted or unsubstituted, saturated orunsaturated ring;

R₃₀₁ to R₃₀₇ and R₃₁₁ to R₃₁₇ that do not form the substituted orunsubstituted, saturated or unsaturated ring are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

R₃₂₁ and R₃₂₂ are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

R₉₀₁ to R₉₀₇ are as defined in the formula (1).

Example of “One pair of two or more adjacent groups of R₃₀₁ to R₃₀₇ andR₃₁₁ to R₃₁₇” is pairs of R₃₀₁ and R₃₀₂, R₃₀₂ and R₃₀₃, R₃₀₃ and R₃₀₄,R₃₀₅ and R₃₀₆, R₃₀₆ and R₃₀₇, and R₃₀₁, R₃₀₂ and R₃₀₃, and the like.

In one embodiment, at least one of R₃₀₁ to R₃₀₇ and R₃₁₁ to R₃₁₇,preferably two of R₃₀₁ to R₃₀₇ and R₃₁₁ to R₃₁₇ is a group representedby —N(R₉₀₆)(R₉₀₇).

In one embodiment, R₃₀₁ to R₃₀₇ and R₃₁₁ to R₃₁₇ are independently ahydrogen atom, a substituted or unsubstituted aryl group having 6 to 50ring carbon atoms, or a substituted or unsubstituted monovalentheterocyclic group having 5 to 50 ring atoms.

In one embodiment, the compound represented by the formula (31) is acompound represented by the following formula (32):

wherein in the formula (32),

one or more pairs of two or more adjacent groups of R₃₃₁ to R₃₃₄ andR₃₄₁ to R₃₄₄ form a substituted or unsubstituted, saturated orunsaturated ring, or do not form a substituted or unsubstitutedsaturated or unsaturated ring;

R₃₃₁ to R₃₃₄ and R₃₄₁ to R₃₄₄ that do not form the substituted orunsubstituted, saturated or unsaturated ring and R₃₅₁ and R₃₅₂ areindependently

a hydrogen atom,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

R₃₆₁ to R₃₆₄ are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms.

In one embodiment, the compound represented by the formula (31) is acompound represented by the formula (33):

wherein in the formula (33), R₃₅₁, R₃₅₂, and R₃₆₁ to R₃₆₄ are as definedin the formula (32).

In one embodiment, the compound represented by the formula (31) is acompound represented by the formula (34) or (35):

wherein in the formulas (34) and (35),

R₃₆₁ to R₃₆₄ are as defined in the formula (32);

one or more pairs of two or more adjacent groups of R₃₇₁ to R₃₇₇ andR₃₈₀ to R₃₈₆ form a substituted or unsubstituted, saturated orunsaturated ring, or do not form a substituted or unsubstitutedsaturated or unsaturated ring; and

R₃₇₁ to R₃₇₇ and R₃₈₀ to R₃₈₆ that do not form the substituted orunsubstituted, saturated or unsaturated ring and R₃₈₇ are independently

a hydrogen atom,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms, two R₃₈₇ may be the same with or different from eachother.

In one embodiment, the compound represented by the formula (31) is acompound represented by the formula (34-2) or (35-2):

wherein in the formulas (34-2) and (35-2), R₃₆₁ to R₃₆₄, R₃₇₅ to R₃₇₇and R₃₈₄ to R₃₈₇ are as defined in the formulas (34) and (35).

In one embodiment, R₃₆₁ to R₃₆₄ in the formulas (32), (33), (34), (35),(34-2) and (35-2) are independently a substituted or unsubstituted arylgroup having 6 to 50 ring carbon atoms (preferably a phenyl group).

In one embodiment, R₃₂₁ and R₃₂₂ in the formula (31), and R₃₅₁ and R₃₅₂in the formulas (32), (33), (34), (35), (34-2) and (35-2) areindependently a hydrogen atom or a substituted or unsubstituted arylgroup having 6 to 50 ring carbon atoms (preferably a phenyl group).

In one embodiment, the compound represented by the formula (31) is thecompound represented by the following formula (36).

In the formula (36),

one or more pairs of two or more adjacent groups of R₃₀₀₁, R₃₀₀₂, R₃₀₀₅to R₃₀₀₇, R₃₀₁₀, R₃₀₁₁, R₃₀₁₄ to R₃₀₁₆ and R₃₀₃₁ to R₃₀₃₄ bond with eachother to form a substituted or unsubstituted, saturated or unsaturatedring or do not form the ring;

X_(a)s are independently selected from O, S and N(R₃₅);

R₃₅ and R₃₀₃₁ bond with each other to form a substituted orunsubstituted, saturated or unsaturated ring or do not form the ring;and

R₃₀₀₁, R₃₀₀₂, R₃₀₀₅ to R₃₀₀₇, R₃₀₁₀, R₃₀₁₁, R₃₀₁₄ to R₃₀₁₆ and R₃₀₃₁ toR₃₀₃₅ that do not form the ring and R₃₀₂₁ and R₃₀₂₂ are independently

a hydrogen atom,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms.

In one embodiment, a substituent in the case of “substituted orunsubstituted” in the formulas (31) to (36) is

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms.

As the compound represented by the formula (31), the following compoundscan be given for example. In the following example compounds, Merepresents methyl group.

(Compound Represented by Formula (41))

The compound represented by the formula (41) is explained below.

In the formula (41),

a ring, b ring and c ring are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50ring carbon atoms, ora substituted or unsubstituted heterocyclic ring having 5 to 50 ringatoms;

R₄₀₁ and R₄₀₂ are independently bonded to the a ring, the b ring or thec ring to form a substituted or unsubstituted heterocyclic ring or donot form a substituted or unsubstituted heterocyclic ring;

R₄₀₁ and R₄₀₂ that do not form the substituted or unsubstitutedheterocyclic ring are independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms.

The a ring, b ring and c ring are rings (a substituted or unsubstitutedaromatic hydrocarbon ring having 6 to 50 ring carbon atoms or asubstituted or unsubstituted heterocyclic ring having 5 to 50 ringatoms) fuse to the fused bicyclic structure composed of B atom and two Natoms in the center of the formula (41).

The “aromatic hydrocarbon ring” of the a ring, the b ring and the c ringhas the same structure as the compound obtained by introducing ahydrogen atom into the “aryl group” described above. The “aromatichydrocarbon ring” of the a ring contains three carbon atoms in the fusedbicyclic structure in the center of the formula (41) as ring atoms. The“aromatic hydrocarbon ring” of the b ring and the c ring contain twocarbon atoms in the fused bicyclic structure in the center of theformula (41) as ring atoms. As examples of “substituted or unsubstitutedaromatic hydrocarbon ring having 6 to 50 ring carbon atoms”, compoundsin which a hydrogen atom is introduced into the “aryl group” describedin the group G1 and the like can be given. The “heterocyclic ring” ofthe a ring, the b ring and the c ring has the same structure as thecompound obtained by introducing a hydrogen atom into the “heterocyclicgroup” described above. The “heterocyclic ring” of the a ring containsthree carbon atoms in the fused bicyclic structure in the center of theformula (41) as ring atoms. The “heterocyclic ring” of the b ring andthe c ring contain two carbon atoms in the fused bicyclic structure inthe center of the formula (41) as ring atoms. As examples of“substituted or unsubstituted heterocyclic ring having 5 to 50 ringatoms”, compounds in which a hydrogen atom is introduced into the“heterocyclic group” described in the group G2.

R₄₀₁ and R₄₀₂ may be independently bonded to the a ring, the b ring orthe c ring to form a substituted or unsubstituted heterocyclic ring.This heterocyclic ring contains the nitrogen atom in the fused bicyclicstructure in the center of the formula (41). This heterocyclic ring maycontain a heteroatom other than the nitrogen atom. “R₄₀₁ and R₄₀₂ arebonded to the a ring, the b ring or the c ring” means, specifically, anatom forming the a ring, the b ring or the c ring is bonded to an atomforming R₄₀₁ and R₄₀₂. For example, it is possible that R₄₀₁ is bondedto the a ring to form a nitrogen-containing heterocyclic ring having atwo-ring fused structure (or three or more rings fused structure) inwhich a ring containing R₄₀₁ and the a ring are fused. Specific examplesof the nitrogen-containing heterocyclic ring include compound and thelike corresponding to a heterocyclic group of 2 ring condensation ormore containing nitrogen among specific example groups G2. The sameapplies to the case where R₄₀₁ is bonded to the b ring, R₄₀₂ is bondedto the a ring, and R₄₀₂ is bonded to the c ring.

In one embodiment, the a ring, the b ring and the c ring in the formula(41) are independently a substituted or unsubstituted aromatichydrocarbon ring having 6 to 50 ring carbon atoms.

In one embodiment, the a ring, the b ring and the c ring in the formula(41) are independently a substituted or unsubstituted benzene ring or asubstituted or unsubstituted naphthalene ring.

In one embodiment, R₄₀₁ and R₄₀₂ in the formula (41) are independently asubstituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or a substituted or unsubstituted monovalent heterocyclic grouphaving 5 to 50 ring atoms, and preferably a substituted or unsubstitutedaryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the formula (41) is acompound represented by the following formula (42):

wherein in the formula (42),

R_(401A) is bonded with one or more groups selected from R₄₁₁ or R₄₂₁ toform a substituted or unsubstituted heterocyclic ring, or does not forma substituted or unsubstituted heterocyclic ring; R_(402A) is bondedwith one or more group selected from R₄₁₃ or R₄₁₄ to form a substitutedor unsubstituted heterocyclic ring, or does not form a substituted orunsubstituted heterocyclic ring;

R_(401A) and R_(402A) that do not form a substituted or unsubstitutedheterocyclic ring are independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

One or more pairs of two or more adjacent groups of R₄₁₁ to R₄₂₁ arebonded with each other to form a substituted or unsubstituted, saturatedor unsaturated ring, or do not form a substituted or unsubstituted,saturated or unsaturated ring;

R₄₁₁ to R₄₂₁ that do not form the substituted or unsubstitutedheterocyclic ring or the substituted or unsubstituted, saturated orunsaturated ring are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

R₉₀₁ to R₉₀₇ are as defined in the formula (1).

R_(401A) and R_(402A) in the formula (42) correspond to R₄₀₁ and R₄₀₂ inthe formula (41). R_(401A) and R₄₁₁ may be bonded with each other toform a nitrogen-containing heterocyclic ring having two-ring fusedstructure (or three or more rings fused structure) which is a fused ringof a ring containing R_(401A) and R₄₁₁ and the benzene ring of the aring, for example. As examples of the nitrogen-containing heterocyclicring, compounds correspond to nitrogen-containing heterocyclic grouphaving two or more ring fused structure in the group G2 can be given.The same applies to the cases where R_(401A) and R₄₁₂ are bonded,R_(402A) and R₄₁₃ are bonded, and R_(402A) and R₄₁₄ are bonded.

One or more pairs of two or more adjacent groups of R₄₁₁ to R₄₂₁ arebonded with each other to form a substituted or unsubstituted, saturatedor unsaturated ring. For example, R₄₁₁ and R₄₁₂ are bonded to form abenzene ring, an indole ring, a pyrrole ring, a benzofuran ring, abenzothiophene ring or the like which fuses to the six-membered ring towhich R₄₁₁ and R₄₁₂ bond, and the formed fused ring is a naphthalenering, a carbazole ring, an indole ring, a dibenzofuran ring or adibenzothiophene ring.

In one embodiment, R₄₁₁ to R₄₂₁ that do not contribute to form a ringare independently a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, a substituted or unsubstituted arylgroup having 6 to 50 ring carbon atoms, or a substituted orunsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R₄₁₁ to R₄₂₁ that do not contribute to form a ringare independently a hydrogen atom, a substituted or unsubstituted arylgroup having 6 to 50 ring carbon atoms, or a substituted orunsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R₄₁₁ to R₄₂₁ that do not contribute to form a ringare independently a hydrogen atom or a substituted or unsubstitutedalkyl group having 1 to 50 carbon atoms.

In one embodiment, R₄₁₁ to R₄₂₁ that do not contribute to form a ringare independently a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, and at least one of R₄₁₁ to R₄₂₁ is asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the formula (42) is acompound represented by the following formula (43):

wherein in the formula (43),

R₄₃₁ is bonded with R₄₄₆ to form a substituted or unsubstitutedheterocyclic ring, or does not form a substituted or unsubstitutedheterocyclic ring; R₄₃₃ is bonded with R₄₄₇ to form a substituted orunsubstituted heterocyclic ring, or does not form a substituted orunsubstituted heterocyclic ring; R₄₃₄ is bonded with R₄₅₁ to form asubstituted or unsubstituted heterocyclic ring, or does not form asubstituted or unsubstituted heterocyclic ring; R₄₄₁ is bonded with R₄₄₂to form a substituted or unsubstituted heterocyclic ring, or does notform a substituted or unsubstituted heterocyclic ring;

One or more pairs of two or more adjacent groups of R₄₃₁ to R₄₅₁ arebonded with each other to form a substituted or unsubstituted, saturatedor unsaturated ring, or do not form a substituted or unsubstituted,saturated or unsaturated ring;

R₄₃₁ to R₄₅₁ that do not form a substituted or unsubstitutedheterocyclic ring are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

R₉₀₁ to R₉₀₇ are as defined in the formula (1).

R₄₃₁ may bond to R₄₄₆ to forma substituted or unsubstituted heterocyclicring. For example, R₄₃₁ may bonds with R₄₄₆ to form anitrogen-containing heterocyclic ring with three or more fused rings ofthe benzene ring to which R₄₆ bond, a nitrogen-containing ring and thebenzene ring of the a ring. As examples of the nitrogen-containingheterocyclic ring, compounds correspond to nitrogen-containingheterocyclic group having three or more ring fused structure in thegroup G2 can be given. The same applies to the cases where R₄₃ and R₄₄₇are bonded, R₄₃₄ and R₄₅₁ are bonded, and R₄₄₁ and R₄₄₂ are bonded.

In one embodiment, R₃₁ to R₄₅₁ that do not contribute to form a ring areindependently, a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, a substituted or unsubstituted arylgroup having 6 to 50 carbon atoms, or a substituted or unsubstitutedmonovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R₄₃₁ to R₄₅₁ that do not contribute to form a ringare independently, a hydrogen atom, a substituted or unsubstituted arylgroup having 6 to 50 carbon atoms, or a substituted or unsubstitutedmonovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R₃₁ to R₄₅₁ that do not contribute to form a ring areindependently a hydrogen atom or a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms.

In one embodiment, R₃₁ to R₄₅₁ that do not contribute to form a ring areindependently a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, and at least one of R₄₃₁ to R₄₅₁ is asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the formula (43) is acompound represented by the following formula (43A):

wherein in the formula (43A),

R₄₆₁ is

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms, ora substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms; and

R₄₆₂ to R₄₆₅ are independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms, ora substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms.

In one embodiment, R₄₆₁ to R₄₆₅ are independently a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms or a substitutedor unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R₄₆₁ and R₄₆₅ are independently a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the formula (43) is acompound represented by the following formula (43B):

wherein in the formula (43B),

R₄₇₁ and R₄₇₂ are independently,

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—N(R₉₀₆)(R₉₀₇), ora substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms;

R₄₇₃ to R₄₇₅ are independently,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—N(R₉₀₆)(R₉₀₇), ora substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms; and

R₉₀₆ and R₉₀₇ are as defined in the formula (1).

In one embodiment, the compound represented by the formula (43) is thecompound represented by the following formula (43B′):

wherein in the formula (43B′), R₄₇₂ to R₄₇₅ are as defined in theformula (43B).

In one embodiment, at least one of R₄₇₁ to R₄₇₅ is

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—N(R₉₀₆)(R₉₀₇), ora substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms.

In one embodiment,

R₄₇₂ is

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,—N(R₉₀₆)(R₉₀₇), ora substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms; and

R₄₇₁ and R₄₇₃ to R₄₇₅ are independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,—N(R₉₀₆)(R₉₀₇), ora substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms.

In one embodiment, the compound represented by the formula (43) is acompound represented by the formula (43C):

wherein in the formula (43C),

R₄₈₁ and R₄₈₂ are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms, ora substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms; and

R₄₈₃ to R₄₈₆ are independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms, ora substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms.

In one embodiment, the compound represented by the formula (43) is thecompound represented by the following formula (43C′):

wherein in the formula (43C′), R₄₈₃ to R₄₈₆ are as defined in theformula (43C).

In one embodiment, R₄₈₁ to R₄₈₆ are independently a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms or a substitutedor unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R₄₈₁ to R₄₈₆ are independently a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms.

The compound represented by the formula (41) can be synthesized by thefollowing method: An intermediate is obtained by bonding the a ring, theb ring and the c ring with linking groups (a group containing N—R₁ and agroup containing N—R₂) (first reaction), and a final compound isobtained by bonding the a ring, the b ring and the c ring with a linkinggroup (a group containing B) (second reaction). In the first reaction,an amination reaction such as Buchwald-Hartwig reaction can be applied.In the second reaction, tandem hetero-Friedel-Crafts reaction or thelike can be applied.

Examples of the compound represented by the formula (41) are describedbelow. They are just exemplified compounds and the compound representedby the formula (41) is not limited to the following examples. In thefollowing example compounds, Me represents methyl group and tBurepresents tert-butyl group.

(Compound Represented by Formula (51))

The compound represented by the formula (51) is explained below.

In the formula (51),

r ring is a ring represented by the formula (52) or formula (53) whichis fused to an adjacent ring at an arbitrary position;

q ring and s ring are independently a ring represented by the formula(54) which is fused to an adjacent ring at an arbitrary position;

p ring and t ring are independently a ring represented by the formula(55) or the formula (56) which is fused to an adjacent ring at anarbitrary position;

when plural R₅₀₁s exist, adjacent plural R₅₀₁s are bonded with eachother to form a substituted or unsubstituted, saturated or unsaturatedring, or do not form a substituted or unsubstituted, saturated orunsaturated ring;

X₅₀₁ is an oxygen atom, a sulfur atom, or NR₅₀₂;

R₅₀₁ and R₅₀₂ that do not form the substituted or unsubstitutedsaturated or unsaturated ring are

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

R₉₀₁ to R₉₀₇ are as defined in the formula (1);

Ar₅₀₁ and Ar₅₀₂ are independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

L₅₀₁ is

a substituted or unsubstituted alkylene group having 1 to 50 carbonatoms,a substituted or unsubstituted alkenylene group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynylene group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkylene group having 3 to 50 ringcarbon atoms,a substituted or unsubstituted arylene group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted divalent heterocyclic group having 5 to50 ring atoms;

m1 is independently an integer of 0 to 2, m2 is independently an integerof 0 to 4, m3 is independently an integer of 0 to 3, and m4 isindependently an integer of 0 to 5; when plural R₅₀₁s exist, the pluralR₅₀₁s may be the same or different;

In the formula (51), each of the p ring to the t ring is fused to anadjacent ring by sharing two carbon atoms. The position and direction offusing are not limited, and condensation is possible at any position anddirection.

In one embodiment, in the formula (52) or (53) of the r ring, R₉₀₁ is ahydrogen atom.

In one embodiment, the compound represented by the formula (51) isrepresented by any one of the following formulas (51-1) to (51-6):

wherein in the formulas (51-1) to (51-6), R₅₀₁, X₅₀₁, Ar₅₀₁, Ar₅₀₂,L₅₀₁, m1 and m3 are as defined in the formula (51).

In one embodiment, the compound represented by the formula (51) isrepresented by any one of the following formulas (51-11) to (51-13):

wherein in the formulas (51-11) to (51-13), R₅₀₁, X₅₀₁, Ar₅₀₁, Ar₅₀₂,L₅₀₁, m1, m3 and m4 are as defined in the formula (51).

In one embodiment, the compound represented by the formula (51) isrepresented by any one of the following formulas (51-21) to (51-25):

wherein in the formulas (51-21) to (51-25), R₅₀₁, X501, Ar₅₀₁, Ar₅₀₂,L₅₀₁, m1 and m4 are as defined in the formula (51).

In one embodiment, the compound represented by the formula (51) isrepresented by any one of the following formulas (51-31) to (51-33):

wherein in the formulas (51-31) to (51-33), R₅₀₁, X501, Ar₅₀₁, Ar₅₀₂,L₅₀₁, m2 to m4 are as defined in the formula (51).

In one embodiment, Ar₅₀₁ and Ar₅₀₂ are independently a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, one of Ar₅₀₁ and Ar₅₀₂ is a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms and the otheris a substituted or unsubstituted monovalent heterocyclic ring having 5to 50 ring atoms.

As examples of the compound represented by the formula (51), thefollowing compounds can be given, for example. In the following examplecompounds, Me represents methyl group.

(Compound Represented by Formula (61))

The compound represented by the formula (61) is explained below.

In the formula (61),

at least one pair of R₆₀₁ and R₆₀₂, R₆₀₂ and R₆₀₃, and R₆₀₃ and R₆₀₄ arebonded with each other to form a divalent group represented by theformula (62);

at least one pair of R₆₀₅ and R₆₀₆, R₆₀₆ and R₆₀₇, and R₆₀₇ and R₆₀₈ arebonded with each other to form a divalent group represented by formula(63);

at least one of R₆₀₁ to R₆₀₄ that does not form the divalent grouprepresented by the formula (62), and R₆₁₁ to R₆₁₄ is a monovalent grouprepresented by the following formula (64);

at least one of R₆₀₅ to R₆₀₈ that do not form the divalent grouprepresented by the formula (63), and R₆₂₁ to R₆₂₄ is a monovalent grouprepresented by the following formula (64);

X₆₀₁ is an oxygen atom, a sulfur atom, or NR₉₀₉;

R₆₀₁ to R₆₀₈ that do not form the divalent group represented by theformulas (62) and (63) and that is not the monovalent group representedby the formula (64), R₆₁₁ to R₆₁₄ and R₆₂₁ to R₆₂₄ that are not themonovalent group represented by the formula (64), and R₆₀₉ areindependently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

R₉₀₁ to R₉₀₇ are as defined in the formula (1);

wherein, in the formula (64), Ar₆₀₁ and Ar₆₀₂ are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

L₆₀₁ to L₆₀₃ are independently

a single bond,a substituted or unsubstituted arylene group having 6 to 30 ring carbonatoms,a substituted or unsubstituted divalent heterocyclic group having 5 to30 ring atoms, ora divalent linking group formed by bonding 2 to 4 above mentionedgroups;

In the formula (61), positions at which the divalent group representedby the formula (62) and the divalent group represented by the formula(63) are formed are not limited, and said groups can be formed atpossible positions in R₆₀₁ to R₆₀₆.

In one embodiment, the compound represented by the formula (61) isrepresented by any one of the following formulas (61-1) to (61-6):

wherein in the formulas (61-1) to (61-6), X₆₀₁ is as defined in theformula (61);

at least two of R₆₀₁ to R₆₂₄ are monovalent groups represented by theformula (64);

R₆₀₁ to R₆₂₄ that are not monovalent groups represented by the formula(64) are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

R₉₀₁ to R₉₀₇ are as defined in the formula (1).

In one embodiment, the compound represented by the formula (61) isrepresented by any one of the following formulas (61-7) to (61-18):

wherein in the formulas (61-7) to (61-18), X₆₀₁ is as defined in theformula (61); * is a single bond bonding to the monovalent grouprepresented by the formula (64); and R₆₀₁ to R₆₂₄ are the same as R₆₀₁to R₆₂₄ that are not monovalent groups represented by the formula (64).

R₆₀, to R₆₀₈ which do not form the divalent group represented by theformula (62) and (63) and are not monovalent groups represented by theformula (64), and R₆₁₁ to R₆₁₄ and R₆₂₁ to R₆₂₄ which are not monovalentgroups represented by the formula (64) are preferably independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms.

The monovalent group represented by the formula (64) is preferablyrepresented by the following formulas (65) or (66):

wherein in the formula (65), R₆₃₁ to R₆₄₀ are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

R₉₀₁ to R₉₀₇ are as defined in the formula (1);

wherein in the formula (66), Ar₆₀₁, L₆₀₁ and L₆₀₃ are as defined in theformula (64); and HAr₆₀₁ is a structure represented by the followingformula (67);

wherein in the formula (67) X₆₀₂ is an oxygen atom or a sulfur atom;

any one of R₆₄₁ to R₆₄₈ is a single bond bonding to L₆₀₃;

R₆₄₁ to R₆₄₈ which are not single bonds are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

R₉₀₁ to R₉₀₇ are as defined in the formula (1).

As specific example of the compound represented by the formula (61), inaddition to the compounds described in WO2014/104144, the followingcompounds can be given, for example. In the following example compounds,Me represents methyl group.

(Compound Represented by Formula (71))

The compound represented by the formula (71) is explained below.

In the formula (71),

A₇₀₁ ring and A₇₀₂ ring are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50ring carbon atoms, ora substituted or unsubstituted heterocyclic ring having 5 to 50 ringatoms;

One or more rings selected from the group consisting of A₇₀₁ ring andA₇₀₂ ring are bonded to the bond * of the structure represented by thefollowing formula (72);

wherein, in the formula (72),

A₇₀₃ rings are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50ring carbon atoms, ora substituted or unsubstituted heterocyclic ring having 5 to 50 ringatoms;

X701 is NR₇₀₃, C(R₇₀₄)(R₇₀₅), Si(R₇₀₆) (R₇₀₇), Ge(R₇₀₈) (R₇₀₉), O, S orSe;

R₇₀₁ and R₇₀₂ are bonded with each other to form a substituted orunsubstituted, saturated or unsaturated ring or do not form asubstituted or unsubstituted saturated or unsaturated ring;

R₇₀₁ and R₇₀₂ that do not form the substituted or unsubstituted,saturated or unsaturated ring, and R₇₀₃ to R₇₀₉ are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

R₉₀₁ to R₉₀₇ are as defined in the formula (1).

One or more selected from the group consisting of A₇₀₁ ring and A₇₀₂ring is bonded to * in the structure represented by the formula (72).That is, in one embodiment, the ring carbon atom of the aromatichydrocarbon ring or the ring atom of the heterocyclic ring of A₇₀₁ ringis bonded to * in the structure represented by the formula (72). In oneembodiment, the ring carbon atom of the aromatic hydrocarbon ring or thering atom of the heterocyclic ring of A₇₀₂ ring is bonded to * in thestructure represented by the formula (72).

In one embodiment, the group represented by the formula (73) is bondedto one or both of A₇₀₁ ring and A₇₀₂ ring:

wherein in the formula (73), Ar₇₀₁ and Ar₇₀₂ are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms; and

L₇₀₁ to L₇₀₃ are independently

a single bond,a substituted or unsubstituted arylene group having 6 to 30 ring carbonatoms,a substituted or unsubstituted divalent heterocyclic group having 5 to30 ring atoms, ora divalent linking group formed by bonding 2 to 4 above mentionedgroups.

In one embodiment, in addition to A₇₀₁ ring, the ring carbon atom of thearomatic hydrocarbon ring or the ring atom of the heterocyclic ring ofA₇₀₂ ring is bonded to * in the structure represented by the formula(72). In this case, the structures represented by formula (72) may bethe same or different.

In one embodiment, R₇₀₁ and R₇₀₂ are independently a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R₇₀₁ and R₇₀₂ are bonded with each other to form afluorene structure.

In one embodiment, Ar₇₀₁ ring and A₇₀₂ ring are substituted orunsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbonatoms, and they are substituted or unsubstituted benzene rings, forexample.

In one embodiment, Ar₇₀₃ ring is a substituted or unsubstituted aromatichydrocarbon ring having 6 to 50 ring carbon atoms, and it is asubstituted or unsubstituted benzene ring, for example.

In one embodiment, X₇₀₁ is O or S.

As specific example of the compound represented by the formula (71), thefollowing compounds can be given, for example. In the following examplecompounds, Me represents methyl group.

(Compound Represented by Formula (81))

The compound represented by the formula (81) is explained below.

In the formula (81),

A₈₀₁ ring is a ring represented by the formula (82) which is fused to anadjacent ring at an arbitrary position;

A₈₀₂ ring is a ring represented by the formula (83) which is fused to anadjacent ring at an arbitrary position;

two bonds * bond to A₈₀₃ ring at an arbitrary position;

X801 and X₈₀₂ are independently C(R₈₀₃)(R₈₀₄), Si(R₈₀₅)(R₈₀₆), an oxygenatom, or a sulfur atom;

A₈₀₃ ring is a substituted or unsubstituted aromatic hydrocarbon ringhaving 6 to 50 ring carbon atoms, or a substituted or unsubstitutedheterocyclic ring having 5 to 50 ring atoms;

Ar₈₀₁ is a substituted or unsubstituted aryl group having 6 to 50 ringcarbon atoms, or a substituted or unsubstituted monovalent heterocyclicgroup having 5 to 50 ring atoms;

R₈₀₁ to R₈₀₆ are independently

a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbonatoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbonatoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄), —S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to50 ring atoms;

R₉₀₁ to R₉₀₇ are as defined in the formula (1);

m801 and m802 are independently an integer of 0 to 2; when these are 2,plural R₈₀₁s or R₈₀₂s may be the same or different;

a801 is an integer of 0 to 2; when a801 is 0 or 1, the structure in theparenthese indicated by “3-a801” may be the same or different from eachother; when a801 is 2, Ar₈₀₁s may be the same or different from eachother.

In one embodiment, A₈₀₁ is a substituted or unsubstituted aryl grouphaving 6 to 50 ring carbon atoms.

In one embodiment, A₈₀₃ ring is a substituted or unsubstituted aromatichydrocarbon ring having 6 to 50 ring carbon atoms, and it is asubstituted or unsubstituted benzene ring, a substituted orunsubstituted naphthalene ring, or a substituted or unsubstitutedanthracene ring, for example.

In one embodiment, R₈₀₃ and R₈₀₄ are independently a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, a801 is 1.

As specific example of the compound represented by the formula (81), thefollowing compounds can be given, for example.

A content of the compound (host material) represented by the formula (1)or (2) in the emitting layer is preferably 80 mass % or more and 99 mass% or less based on the total mass of the emitting layer. A content ofthe one or more compounds (dopant material) selected from the groupconsisting of compounds represented by formulas (11), (21), (31), (41),(51), (61), (71) and (81) is preferably 1 mass % or more and 20 mass %or less based on a total mass of the emitting layer.

Hereinbelow, an explanation will be made on elements and materials otherthan the above-mentioned compound constituting each layer that can beused in the organic EL device according to one aspect of the invention.

(Substrate)

The substrate is used as a supporting body of the emitting device. Asthe substrate, glass, quarts, plastic or the like can be used. Further,a flexible substrate may be used. The flexible substrate means asubstrate that can be bent. For example, a plastic substrate made ofpolycarbonate or vinyl polychloride or the like can be given.

(Anode)

In an anode formed on a substrate, it is preferable to use a metalhaving a large work function (specifically, 4.0 eV or more), an alloy,an electric conductive compound, a mixture of these or the like.Specifically, indium oxide-tin oxide (ITO: Indium Tin Oxide), indiumoxide-tin oxide containing silicon or silicon oxide, indium oxide-zincoxide, tungsten oxide, indium oxide containing zinc oxide, graphene, orthe like can be given. In addition, gold (Au), platinum (Pt) or anitride of a metal material (e.g. titanium nitride) or the like can begiven.

(Hole-Injecting Layer)

The hole-injecting layer is a layer containing a substance having a highhole-injecting property. As a substance having a high hole-injectingproperty, a substance selected from molybdenum oxide, titanium oxide,vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide,zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungstenoxide, manganese oxide, an aromatic amine compound, a polymer compound(oligomer, dendrimer, polymer, etc.) or the like can also be used

(Hole-Transporting Layer)

The hole-transporting layer is a layer containing a substance having ahigh hole-transporting property. For the hole-transporting layer,aromatic amine compounds, carbazole derivatives, anthracene derivativesand the like can be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine)(abbreviation: PVTPA) can also be used. However, any substance otherthan these may be used as long as it is a substance having a highertransporting property for holes than electrons. Note that the layercontaining a substance having a high hole-transporting property is notlimited to a single layer, but may be a stacked body of two or morelayers made of the above substances.

(Guest Material of the Emitting Layer)

The emitting layer is a layer that comprises a substance having highluminous property, and various materials can be used. For example, asthe substance having high luminous property, a fluorescent compound thatemits fluorescent light or a phosphorescent compound that emitsphosphorescent light can be used. The fluorescent compound is a compoundcapable of emitting light from a singlet excited state and thephosphorescent compound is a compound capable of emitting light from atriplet excited state.

As a blue fluorescent material that can be used for the emitting layer,pyrene derivatives, styrylamine derivatives, chrysene derivatives,fluoranthene derivatives, fluorene derivatives, diamine derivatives,triarylamine derivatives and the like can be used. An aromatic aminederivative or the like can be used as a green fluorescent light-emittingmaterial that can be used in the emitting layer. As a red fluorescentmaterial which can be used in emitting layer, a tetracene derivative, adiamine derivative or the like can be used.

Metal complexes such as iridium complexes, osmium complexes, platinumcomplexes and the like are used as the blue phosphorescent material thatcan be used in the emitting layer. An iridium complex or the like isused as a green phosphorescent material that can be used in the emittinglayer. Metal complexes such as iridium complexes, platinum complexes,terbium complexes, europium complexes and the like are used as redphosphorescent materials that can be used in the emitting layer.

(Host Material of Emitting Layer)

The emitting layer may have a structure in which the substance havinghigh luminescent property (guest material) described above is dispersedin another substance (host material). Various materials can be used assubstances for dispersing substances with high luminescent properties,and it is preferable to use a material having a high lowest unoccupiedmolecular orbital level (LUMO level) and a low highest occupiedmolecular orbital level (HOMO level), rather than a material having ahigh luminous property.

As a substance (host material) for dispersing a substance having a highluminous property, 1) a metal complex such as an aluminum complex, aberyllium complex or a zinc complex, 2) a heterocyclic compound such asan oxadiazole derivative, a benzimidazole derivative, a phenanthrolinederivative or the like, 3) a fused aromatic compound such as a carbazolederivative, an anthracene derivative, a phenanthrene derivative, apyrene derivative or a chrysene derivative, and 4) an aromatic aminecompound such as a triarylamine derivative or a fused polycyclicaromatic amine derivative are used.

(Electron-Transporting Layer)

The electron-transporting layer is a layer containing a substance havinga high electron-transporting property. For the electron-transportinglayer, 1) a metal complex such as an aluminum complex, a berylliumcomplex, or a zinc complex, 2) a heteroaromatic compound such as animidazole derivative, a benzimidazole derivative, an azine derivative, acarbazole derivative or a phenanthroline derivative, and 3) a polymercompound can be used.

(Electron-Injecting Layer)

The electron-injection layer is a layer containing a substance having ahigh electron-injection property. For the electron-injection layer,alkali metals, alkaline earth metals or a compound thereof such aslithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride(CsF), calcium fluoride (CaF₂), metal complex compound such as8-quinolinolato lithium (Liq), lithium oxide (LiOx) or the like can beused.

(Cathode)

It is preferable to use a metal, an alloy, an electrically conductivecompound, a mixture thereof, or the like having a small work function(specifically, 3.8 eV or less) for the cathode. Specific examples ofsuch cathode material include elements belonging to Group 1 or Group 2of the periodic table of elements, that is, alkali metals such aslithium (Li) and cesium (Cs), alkaline earth metals such as magnesium(Mg), calcium (Ca), and strontium (Sr),

an alloy containing these metals (for example, MgAg and AlLi), a rareearth metal such as europium (Eu) and ytterbium (Yb), and an alloycontaining a rare earth metal.

In the organic EL device according to one aspect of the invention, themethod for forming each layer is not particularly restricted. Aconventionally known forming method such as a vacuum deposition method,a spin coating method or the like can be used. Each layer such as theemitting layer or the like can be formed by a vacuum deposition method,a molecular beam evaporation method (MBE method), or a known coatingmethod such as a dipping method, a solution spin coating method, acasting method, a bar coating method, or the like, that uses a solutionof a material forming each layer dissolved in a solvent.

In the organic EL device according to one aspect of the invention, thethickness of each layer is not particularly restricted. In general, inorder to suppress occurrence of defects such as pinholes and to suppressthe applied voltage and to improve luminous efficiency, the thickness isnormally preferably in a range of several nm to 1 μm.

[Electronic Device]

The electronic device according to one aspect of the invention ischaracterized in that it is provided with the organic EL deviceaccording to one aspect of the invention.

Specific examples of the electronic device include a display elementsuch as an organic EL panel module; a display such as a TV, a mobilephone or a PC; and emitting devices such as lightings and lights forautomobiles or the like.

EXAMPLES

The invention will specifically be explained with the examples and thecomparative examples below, and shall not be limited to the contents ofthe examples in any way.

Synthesis Example 1 [Synthesis of Compound BH-1] (Synthesis ofIntermediate 1)

To 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 6.4 g (52.5 mmol) ofphenylboronic acid and 1.2 g (1.00 mmol) of Pd[PPh₃]₄, 75 ml of toluene,75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2M Na₂CO₃ aqueoussolution were added under an atmosphere of argon, followed by beingheated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 10.9 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Intermediate 1 as follows (yield:83%).

(Synthesis of Intermediate 2)

5.3 g (20.0 mmol) of Intermediate 1 was solubilized in 120 ml ofdichloromethane, and the resulting solution was dropped into thesolution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane atroom temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to aseparating funnel and washed with 2M Na₂S₂O₃ aqueous solution. Theorganic phase was further washed with 10% Na₂CO₃, and thereafter withwater, and the separated organic phase was dried with MgSO₄, followed bybeing filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL), and theprecipitated crystal was dried to obtain 6.5 g of white solid. Byconducting FD-MS analysis, the resulting compound was identified asIntermediate 2 as follows (yield: 95%).

(Synthesis of Compound BH-1)

To 1.7 g (5.0 mmol) of Intermediate 2, 1.1 g (5.3 mmol) ofdibenzofuran-2-boronic acid and 0.1 g (0.1 mmol) of Pd[PPh₃]4, 7.5 ml oftoluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 1.6 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-1 as follows (yield:75%).

Synthesis Example 2 [Synthesis of Compound BH-2] (Synthesis ofIntermediate 3)

To 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 9.0 g (52.5 mmol) of1-naphthalene boronic acid and 1.2 g (1.00 mmol) of Pd[PPh₃]₄, 75 ml oftoluene, 75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 13.3 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Intermediate 3 as follows (yield:85%).

(Synthesis of Intermediate 4)

6.3 g (20.0 mmol) of Intermediate 3 was solubilized in 120 ml ofdichloromethane, and the resulting solution was dropped into thesolution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane atroom temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to aseparating funnel and washed with 2M Na₂S₂O₃ aqueous solution. Theorganic phase was further washed with 10% Na₂CO₃, and thereafter withwater three times. The organic phase was dried with MgSO₄, followed bybeing filtered and concentrated.

The concentrated residue was dispersed in methanol (100 ml), and theprecipitated crystal was dried to obtain 7.5 g of white solid. Byconducting FD-MS analysis, the resulting compound was identified asIntermediate 4 as follows (yield: 96%).

(Synthesis of Compound BH-2)

To 2.0 g (5.0 mmol) of Intermediate 4, 1.1 g (5.3 mmol) ofdibenzofuran-2-boronic acid and 0.1 g (0.1 mmol) of Pd[PPh₃]₄, 7.5 ml oftoluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 1.7 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-2 as follows (yield:70%).

Synthesis Example 3 [Synthesis of Compound BH-3]

Except that 1.1 g (5.3 mmol) of dibenzofuran-1-boronic acid was usedinstead of dibenzofuran-2-boronic acid, the reaction was carried out inthe same way as in the synthesis example 1, thereby obtaining 1.3 g ofwhite crystal. By conducting FD-MS analysis, the resulting compound wasidentified as Compound BH-3 as follows (yield: 62%).

Synthesis Example 4 [Synthesis of Compound BH-4]

Except that 1.5 g (5.3 mmol) of 4-(2-dibenzofuranyl) phenyl boronic acidwas used instead of dibenzofuran-2-boronic acid, the reaction wascarried out in the same way as in the synthesis example 1, therebyobtaining 1.8 g of white crystal. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-4 as follows (yield:71%).

Synthesis Example 5 [Synthesis of Compound BH-5]

Except that 1.5 g (5.3 mmol) of 4-(2-dibenzofuranyl) phenyl boronic acidwas used instead of dibenzofuran-2-boronic acid, the reaction wascarried out in the same way as in the synthesis example 2, therebyobtaining 2.0 g of white crystal. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-5 as follows (yield:73%).

Synthesis Example 6 [Synthesis of Compound BH-6] (Synthesis ofIntermediate 5)

To 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 10.4 g (52.5 mmol) of4-biphenylboronic acid and 1.2 g (1.00 mmol) of Pd[PPh₃]₄, 75 ml oftoluene, 75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 14.1 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Intermediate 5 as follows (yield:83%).

(Synthesis of Intermediate 6)

6.8 g (20.0 mmol) of Intermediate 5 was solubilized in 120 ml ofdichloromethane, and the resulting solution was dropped into thesolution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane atroom temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to aseparating funnel and washed with 2M Na₂S₂O₃ aqueous solution. Theorganic phase was further washed with 10% Na₂CO₃, and thereafter withwater three times. The organic phase was dried with MgSO₄, followed bybeing filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL), and theprecipitated crystal was dried to obtain 8.0 g of white solid. Byconducting FD-MS analysis, the resulting compound was identified asIntermediate 6 as follows (yield: 96%).

(Synthesis of Compound BH-6)

To 2.1 g (5.0 mmol) of Intermediate 6, 1.1 g (5.3 mmol) ofdibenzofuran-2-boronic acid and 0.1 g (0.1 mmol) of Pd[PPh₃]₄, 7.5 ml oftoluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 1.6 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-6 as follows (yield:64%).

Synthesis Example 7 [Synthesis of Compound BH-7] (Synthesis ofIntermediate 7)

To 13.3 g (50.0 mmol) of 9-bromoanthracene d9, 10.4 g (52.5 mmol) of3-biphenylboronic acid and 1.2 g (1.00 mmol) of Pd[PPh₃]4, 75 ml oftoluene, 75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 13.6 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Intermediate 7 as follows (yield:80%).

(Synthesis of Intermediate 8)

6.8 g (20.0 mmol) of Intermediate 7 was solubilized in 120 ml ofdichloromethane, and the resulting solution was dropped into thesolution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane atroom temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to aseparating funnel and washed with 2M Na₂S₂O₃ aqueous solution. Theorganic phase was further washed with 10% Na₂CO₃, and thereafter withwater three times. The organic phase was dried with MgSO₄, followed bybeing filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL), and theprecipitated crystal was dried to obtain 8.0 g of white solid. Byconducting FD-MS analysis, the resulting compound was identified asIntermediate 8 as follows (yield: 96%).

(Synthesis of Compound BH-7)

To 2.1 g (5.0 mmol) of Intermediate 8, 1.1 g (5.3 mmol) ofdibenzofuran-2-boronic acid and 0.1 g (0.1 mmol) of Pd[PPh₃]4, 7.5 ml oftoluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 1.5 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-7 as follows (yield:59%).

Synthesis Example 8 [Synthesis of Compound BH-8] (Synthesis ofIntermediate 9)

To 13.3 g (50.0 mmol) of 9-bromoanthracene d9, 10.4 g (52.5 mmol) of2-biphenylboronic acid and 1.2 g (1.00 mmol) of Pd[PPh₃]₄, 75 ml oftoluene, 75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 10.9 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Intermediate 9 as follows (yield:64%).

(Synthesis of Intermediate 10)

6.8 g (20.0 mmol) of Intermediate 9 was solubilized in 120 ml ofdichloromethane, and the resulting solution was dropped into thesolution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane atroom temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to aseparating funnel and washed with 2M Na₂S₂O₃ aqueous solution. Theorganic phase was further washed with 10% Na₂CO₃, and thereafter withwater three times. The organic phase was dried with MgSO₄, followed bybeing filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL), and theprecipitated crystal was dried to obtain 8.0 g of white solid. Byconducting FD-MS analysis, the resulting compound was identified asIntermediate 10 as follows (yield: 96%).

(Synthesis of Compound BH-8)

To 2.1 g (5.0 mmol) of Intermediate 10, 1.1 g (5.3 mmol) ofdibenzofuran-2-boronic acid and 0.1 g (0.1 mmol) of Pd[PPh₃]₄, 7.5 ml oftoluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 1.6 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-8 as follows (yield:63%).

Synthesis Example 9 [Synthesis of Compound BH-9] (Synthesis ofIntermediate 11)

To 13.3 g (50.0 mmol) of 9-bromoanthracene d9, 13.0 g (52.5 mmol) of4-(1-naphthyl) phenylboronic acid and 1.2 g (1.00 mmol) of Pd[PPh₃]₄, 75ml of toluene, 75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2MNa₂CO₃ aqueous solution were added under an atmosphere of argon,followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 15.6 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Intermediate 11 as follows (yield:80%).

(Synthesis of Intermediate 12)

7.8 g (20.0 mmol) of Intermediate 11 was solubilized in 120 ml ofdichloromethane, and the resulting solution was dropped into thesolution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane atroom temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to aseparating funnel and washed with 2M Na₂S₂O₃ aqueous solution. Theorganic phase was further washed with 10% Na₂CO₃, and thereafter withwater three times. The organic phase was dried with MgSO₄, followed bybeing filtered and concentrated.

The concentrated residue was dispersed in methanol (100 ml), and theprecipitated crystal was dried to obtain 8.6 g of white solid. Byconducting FD-MS analysis, the resulting compound was identified asIntermediate 12 as follows (yield: 92%).

(Synthesis of Compound BH-9)

To 2.3 g (5.0 mmol) of Intermediate 12, 1.1 g (5.3 mmol) ofdibenzofuran-2-boronic acid and 0.1 g (0.1 mmol) of Pd[PPh₃]₄, 7.5 ml oftoluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 1.9 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-10 as follows (yield:68%).

Synthesis Example 10 [Synthesis of Compound BH-10]

Except that 1.8 g (5.3 mmol) of4-(2-dibenzofuranyl)-1-naphthalenyl-boronic acid was used instead ofdibenzofuran-2-boronic acid, the reaction was carried out in the sameway as in the synthesis example 1, thereby obtaining 1.7 g of whitecrystal. By conducting FD-MS analysis, the resulting compound wasidentified as Compound BH-10 as follows (yield: 60%).

Synthesis Example 11 [Synthesis of Compound BH-11]

Except that 1.8 g (5.3 mmol) of6-(2-dibenzofuranyl)-2-naphthalenyl-boronic acid was used instead ofdibenzofuran-2-boronic acid, the reaction was carried out in the sameway as in the synthesis example 1, thereby obtaining 1.5 g of whitecrystal. By conducting FD-MS analysis, the resulting compound wasidentified as Compound BH-11 as follows (yield: 55%).

Synthesis Example 12 [Synthesis of Compound BH-12]

Except that 1.8 g (5.3 mmol) of6-(2-dibenzofuranyl)-2-naphthalenyl-boronic acid was used instead ofdibenzofuran-2-boronic acid, the reaction was carried out in the sameway as in the synthesis example 2, thereby obtaining 2.0 g of whitecrystal. By conducting FD-MS analysis, the resulting compound wasidentified as Compound BH-12 as follows (yield: 65%).

Synthesis Example 13 [Synthesis of Compound BH-13]

Except that 1.5 g (5.3 mmol) of 3-(2-dibenzofuranyl) phenylboronic acidwas used instead of dibenzofuran-2-boronic acid, the reaction wascarried out in the same way as in the synthesis example 1, therebyobtaining 1.3 g of white crystal. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-13 as follows (yield:52%).

Synthesis Example 14 [Synthesis of Compound BH-14]

Except that 1.5 g (5.3 mmol) of 3-(2-dibenzofuranyl) phenylboronic acidwas used instead of dibenzofuran-2-boronic acid, the reaction wascarried out in the same way as in the synthesis example 2, therebyobtaining 1.4 g of white crystal. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-14 as follows (yield:50%).

Synthesis Example 15 [Synthesis of Compound BH-15]

Except that 1.5 g (5.3 mmol) of 4-(1-dibenzofuranyl) phenylboronic acidwas used instead of dibenzofuran-2-boronic acid, the reaction wascarried out in the same way as in the synthesis example 1, therebyobtaining 1.6 g of white crystal. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-15 as follows (yield:62%).

Synthesis Example 16 [Synthesis of Compound BH-16] (Synthesis ofIntermediate 13)

To 1.33 g (5.00 mmol) of 9-bromoanthracene-d9, 0.67 g (5.25 mmol) ofphenyl-d5-boronic acid and 0.12 g (0.10 mmol) of Pd[PPh₃]₄, 7.5 ml oftoluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 1.07 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Intermediate 13 as follows (yield:80%).

(Synthesis of Intermediate 14)

1.07 g (4.0 mmol) of Intermediate 13 was solubilized in 25 ml ofdichloromethane, and the resulting solution was dropped into thesolution of 0.64 g (4.0 mmol) of bromine in 3 ml of dichloromethane atroom temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to aseparating funnel and washed with 2M Na₂S₂O₃ aqueous solution. Theorganic phase was further washed with 10% Na₂CO₃, and thereafter withwater. The organic phase was dried with MgSO₄, followed by beingfiltered and concentrated.

The concentrated residue was dispersed in methanol (100 ml), and theprecipitated crystal was dried to obtain 1.3 g of white solid. Byconducting FD-MS analysis, the resulting compound was identified asIntermediate 14 as follows (yield: 95%).

(Synthesis of Compound BH-16)

To 0.87 g (2.5 mmol) of Intermediate 14, 0.58 g (2.65 mmol) ofdibenzofuran d7-2-boronic acid and 0.06 g (0.05 mmol) of Pd[PPh₃]₄, 5 mlof toluene, 5 ml of dimethoxyethane and 5 ml (10.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed bybeing heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to roomtemperature, the sample was transferred to a separating funnel andextracted with dichloromethane. The resulting organic phase was driedwith MgSO₄, followed by being filtered and concentrated. Theconcentrated residue was purified with silica gel column chromatographyto obtain 0.77 g of white solid. By conducting FD-MS analysis, theresulting compound was identified as Compound BH-16 as follows (yield:70%).

Example 1 [Fabrication and Evaluation of Organic EL Device] (Fabricationof Organic EL Device)

A glass substrate of 25 mm by 75 mm by 1.1 mm thick with an ITOtransparent electrode (anode) (manufactured by GEOMATEC Co., Ltd.) wassubjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, andthen subjected to UV-ozone cleaning for 30 minutes. The thickness of ITOwas 130 nm.

The cleaned glass substrate with a transparent electrode was mounted ina substrate holder of a vacuum vapor deposition apparatus. First,compound HI was deposited on the surface where the transparent electrodewas formed so as to cover the transparent electrode, thereby forming anHI film having a thickness of 5 nm. This HI film functioned as ahole-injecting layer.

Subsequent to the formation of the HI film, compound HT-1 was depositedto form an HT-1 film in a thickness of 80 nm on the HI film. This HT-1film functioned as a hole-transporting layer (a first hole-transportinglayer).

Subsequent to the formation of the HT-1 film, compound HT-2 wasdeposited to form an HT-2 film in a thickness of 10 nm on the HT-1 film.This HT-2 film functioned as an electron-blocking layer (a secondhole-transporting layer).

Compound BH-1 (host material) and compound BD-1 (dopant material) wereco-deposited on the HT-2 film so that the ratio of compound BD-1 was 4mass % to form a BH-1:BD-1 film in a thickness of 25 nm. This BH-1:BD-1film functioned as an emitting layer.

Compound ET-1 was deposited on the emitting layer to form an ET-1 filmin a thickness of 10 nm. This ET-1 film functioned as a hole-barrierlayer.

Compound ET-2 was deposited on the ET-1 layer to form an ET-2 layer in athickness of 15 nm. This ET-2 layer functioned as anelectron-transporting layer. LiF was deposited on the ET-2 layer to forma LiF film in a thickness of 1 nm. Al metal was deposited on the LiFfilm to form a metal cathode in a thickness of 80 nm. An organic ELdevice was thus fabricated.

The layer construction of the fabricated organic EL device was asfollows.

ITO (130)/HI (5)/HT-1 (80)/HT-2 (10)/BH-1:BD-1 (25:4 mass %)/ET-1(10)/ET-2 (15)/LiF (1)/Al (80)

The numbers in the parenthesis denote the thickness of each layer (unit:nm).

The compounds used in Example 1 as well as the subsequent examples andcomparative examples are shown below.

(Evaluation of Organic EL Device)

A voltage was applied to the obtained organic EL device so that thecurrent density was 50 mA/cm² and the time until the luminance reached95% with respect to the initial luminance (LT95) was measured. Theresults are shown in Table 1.

Further a voltage was applied to the obtained organic EL device so thatthe current density was 10 mA/cm², and spectral radiance spectrum wasmeasured using a spectroradiometer “CS-1000” (manufactured by KonicaMinolta, Inc.) to determine CIE1931 chromaticity coordinate (CIEx,CIEy). The results are shown in Table 1.

Comparative Examples 1-1 and 1-2

Except that the compound shown in the following table was used as thehost material of the emitting layer, the organic EL device wasfabricated and evaluated in the same manner as in Example 1. The resultsare shown in Table 1.

TABLE 1 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 1 BH-1 BD-1 155 0.139 0.090 Comp. Ex. 1-1BH-1-a BD-1 94 0.139 0.090 Comp. Ex. 1-2 BH-1-b BD-1 95 0.139 0.090

Example 2, Comparative Example 2

Except that the compounds shown in the following table were used as thematerial of the emitting layer, the organic EL devices were fabricatedand evaluated in the same manner as in Example 1. The results are shownin Table 2.

TABLE 2 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 2 BH-2 BD-1 80 0.139 0.090 Comp. Ex. 2 BH-2-aBD-1 49 0.139 0.090

Example 3, Comparative Example 3

Except that the compounds shown in the following table were used as thehost material of the emitting layer, the organic EL devices werefabricated and evaluated in the same manner as in Example 1. The resultsare shown in Table 3.

TABLE 3 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 3 BH-3 BD-1 70 0.139 0.090 Comp. Ex. 3 BH-3-aBD-1 40 0.139 0.090

Example 4, Comparative Examples 4-1 and 4-2

Except that the compounds shown in the following table were used as thehost material of the emitting layer, the organic EL devices werefabricated and evaluated in the same manner as in Example 1. For organicEL device obtained in Example 4 and Comparative Example 4-2, the drivingvoltages at the time of driving Here measured at room temperature 10mA/cm²a DC (direct current) constant current. The results are shown inTable 4.

TABLE 4 Emitting layer Host Dopant Chromaticity material materialLT95(h) ClEx CIEy Voltage(V) Example 4 BH-4 BD-1 170 0.139 0.091 3.7Comp. Ex. 4-1 BH-4-a BD-1 101 0.139 0.091 — Comp. Ex. 4-2 BH-4-b BD-1120 0.139 0.090 4.1

Example 5, Comparative Examples 5-1 and 5-2

Except that the compound shown in the following table was used as thehost material of the emitting layer, the organic EL device wasfabricated and evaluated in the same manner as in Example 1. The resultsare shown in Table 5.

TABLE 5 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 5 BH-5 BD-1 145 0.139 0.090 Comp. Ex. 5-1BH-5-a BD-1 89 0.139 0.090 Comp. Ex. 5-2 BH-5-b BD-1 85 0.139 0.090

Example 11, Comparative Example 11

Except that the compound shown in the following table was used as thehost material and the dopant material of the emitting layer, the organicEL device was fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 6.

TABLE 6 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 11 BH-1 BD-2 130 0.140 0.080 Comp. Ex. 11BH-1-a BD-2 83 0.140 0.080

Example 12, Comparative Example 12

Except that the compound shown in the following table was used as thehost material and the dopant material of the emitting layer, the organicEL device was fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 7.

TABLE 7 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 12 BH-2 BD-2 71 0.140 0.081 Comp. Ex. 12BH-2-a BD-2 45 0.140 0.080

Example 13, Comparative Example 13

Except that the compound shown in the following table was used as thehost material and the dopant material of the emitting layer, the organicEL device was fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 8.

TABLE 8 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 13 BH-3 BD-2 56 0.140 0.080 Comp. Ex. 13BH-3-a BD-2 36 0.140 0.080

Example 14, Comparative Example 14

Except that the compound shown in the following table was used as thehost material and the dopant material of the emitting layer, the organicEL device was fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 9.

TABLE 9 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 14 BH-4 BD-2 146 0.140 0.080 Comp. Ex. 14BH-4-a BD-2 82 0.140 0.080

Example 15, Comparative Example 15

Except that the compound shown in the following table was used as thehost material and the dopant material of the emitting layer, the organicEL device was fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 10.

TABLE 10 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 15 BH-5 BD-2 126 0.140 0.080 Comp. Ex. 15BH-5-a BD-2 78 0.140 0.080

Example 16, Comparative Example 16

Except that the compound shown in the following table was used as thehost material and the dopant material of the emitting layer, the organicEL device was fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 11.

TABLE 11 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 16 BH-6 BD-2 127 0.140 0.080 Comp. Ex. 16BH-6-a BD-2 80 0.140 0.080

Example 21, Comparative Example 21

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 12.

TABLE 12 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 21 BH-1 BD-3 155 0.135 0.098 Comp. Ex. 21BH-1-a BD-3 96 0.135 0.098

Example 22, Comparative Example 22

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 13.

TABLE 13 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 22 BH-2 BD-3 77 0.135 0.098 Comp. Ex. 22BH-2-a BD-3 50 0.135 0.099

Example 23, Comparative Example 23

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 14.

TABLE 14 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 23 BH-3 BD-3 73 0.135 0.098 Comp. Ex. 23BH-3-a BD-3 43 0.135 0.098

Example 24, Comparative Example 24

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 15.

TABLE 15 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 24 BH-4 BD-3 167 0.135 0.098 Comp. Ex. 24BH-4-a BD-3 105 0.135 0.098

Example 25, Comparative Example 25

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 16.

TABLE 16 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 25 BH-5 BD-3 147 0.135 0.098 Comp. Ex. 25BH-5-a BD-3  92 0.135 0.098

Example 26, Comparative Example 26

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 17.

TABLE 17 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 26 BH-6 BD-3 150 0.135 0.098 Comp. Ex. 26BH-6-a BD-3  96 0.135 0.098

Example 31, Comparative Example 31

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 18.

TABLE 18 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 31 BH-1 BD-4 163 0.135 0.086 Comp. Ex. 31BH-1-a BD-4  98 0.135 0.086

Example 32, Comparative Example 32

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 19.

TABLE 19 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 32 BH-2 BD-4 78 0.135 0.086 Comp. Ex. 32BH-2-a BD-4 51 0.135 0.086

Example 33, Comparative Example 33

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 20.

TABLE 20 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 33 BH-3 BD-4 73 0.135 0.086 Comp. Ex. 33BH-3-a BD-4 39 0.135 0.086

Example 34, Comparative Example 34

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 21.

TABLE 21 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 34 BH-4 BD-4 170 0.135 0.086 Comp. Ex. 34BH-4-a BD-4 105 0.135 0.086

Example 35, Comparative Example 35

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 22.

TABLE 22 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 35 BH-5 BD-4 152 0.135 0.086 Comp. Ex. 35BH-5-a BD-4  89 0.135 0.086

Example 36, Comparative Example 36

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 23.

TABLE 23 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 36 BH-6 BD-4 161 0.135 0.086 Comp. Ex. 36BH-6-a BD-4 102 0.135 0.086

Example 41, Comparative Example 41

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 24.

TABLE 24 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 41 BH-1 BD-5 195 0.135 0.080 Comp. Ex. 41BH-1-a BD-5 123 0.135 0.080

Example 42, Comparative Example 42

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 25.

TABLE 25 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 42 BH-2 BD-5 106 0.135 0.080 Comp. Ex. 42BH-2-a BD-5  66 0.135 0.080

Example 43, Comparative Example 43

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 26.

TABLE 26 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 43 BH-3 BD-5 90 0.135 0.080 Comp. Ex. 43BH-3-a BD-5 53 0.135 0.080

Example 44, Comparative Example 44

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 27.

TABLE 27 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 44 BH-4 BD-5 211 0.135 0.080 Comp. Ex. 44BH-4-a BD-5 133 0.135 0.081

Example 45, Comparative Example 45

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 28.

TABLE 28 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 45 BH-5 BD-5 179 0.135 0.080 Comp. Ex. 45BH-5-a BD-5 112 0.135 0.080

Example 46, Comparative Example 46

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 29.

TABLE 29 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 46 BH-6 BD-5 202 0.135 0.080 Comp. Ex. 46BH-6-a BD-5 125 0.135 0.080

Example 51, Comparative Example 51

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 30.

TABLE 30 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 51 BH-1 BD-6 253 0.136 0.090 Comp. Ex. 51BH-1-a BD-6 146 0.136 0.090

Example 52, Comparative Example 52

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 31.

TABLE 31 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 52 BH-2 BD-6 125 0.136 0.090 Comp. Ex. 52BH-2-a BD-6 73 0.136 0.090

Example 53, Comparative Example 53

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 32.

TABLE 32 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 53 BH-3 BD-6 102 0.136 0.090 Comp. Ex. 53BH-3-a BD-6 64 0.136 0.090

Example 54, Comparative Example 54

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 33.

TABLE 33 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 54 BH-4 BD-6 257 0.136 0.090 Comp. Ex. 54BH-4-a BD-6 161 0.136 0.091

Example 55, Comparative Example 55

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 34.

TABLE 34 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 55 BH-5 BD-6 215 0.136 0.090 Comp. Ex. 55BH-5-a BD-6 137 0.136 0.090

Example 56, Comparative Example 56

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 35.

TABLE 35 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 56 BH-6 BD-6 241 0.136 0.090 Comp. Ex. 56BH-6-a BD-6 141 0.136 0.090

Example 61, Comparative Example 61

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 36.

TABLE 36 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 61 BH-1 BD-7 104 0.144 0.061 Comp. Ex. 61BH-1-a BD-7 65 0.144 0.061

Example 62, Comparative Example 62

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 37.

TABLE 37 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 62 BH-2 BD-7 53 0.144 0.061 Comp. Ex. 62BH-2-a BD-7 37 0.144 0.061

Example 63, Comparative Example 63

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 38.

TABLE 38 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 63 BH-3 BD-7 51 0.144 0.060 Comp. Ex. 63BH-3-a BD-7 32 0.144 0.061

Example 64, Comparative Example 64

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 39.

TABLE 39 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 64 BH-4 BD-7 117 0.144 0.061 Comp. Ex. 64BH-4-a BD-7 75 0.144 0.061

Example 65, Comparative Example 65

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 40.

TABLE 40 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 65 BH-5 BD-7 105 0.144 0.061 Comp. Ex. 65BH-5-a BD-7 65 0.144 0.061

Example 66, Comparative Example 66

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 41.

TABLE 41 Emitting layer Host Dopant Chromaticity material materialLT95(h) CIEx CIEy Example 66 BH-6 BD-7 110 0.144 0.061 Comp. Ex. 66BH-6-a BD-7 66 0.144 0.061

Example 71, Comparative Example 71

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 42.

TABLE 42 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 71 BH-6 BD-1 154 0.139 0.090 Comp. Ex. 71 BH-6-aBD-1  90 0.139 0.090

Example 72, Comparative Example 72

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 43.

TABLE 43 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 72 BH-7 BD-1 116 0.139 0.090 Comp. Ex. 72 BH-7-aBD-1  70 0.139 0.090

Example 73, Comparative Example 73

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 44.

TABLE 44 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 73 BH-8 BD-1 110 0.139 0.090 Comp. Ex. 73 BH-8-aBD-1  75 0.139 0.090

Example 74, Comparative Example 74

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 45.

TABLE 45 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 74 BH-9 BD-1 110 0.139 0.090 Comp. Ex. 74 BH-9-aBD-1  70 0.139 0.090

Example 75, Comparative Example 75

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 46.

TABLE 46 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 75 BH-10 BD-1 103 0.139 0.090 Comp. Ex. 75 BH-10-aBD-1  58 0.139 0.090

Example 76, Comparative Example 76

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 47.

TABLE 47 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 76 BH-11 BD-1 95 0.139 0.090 Comp. Ex. 76 BH-11-aBD-1 50 0.139 0.090

Example 77, Comparative Example 77

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 48.

TABLE 48 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 77 BH-12 BD-1 75 0.139 0.090 Comp. Ex. 77 BH-12-aBD-1 51 0.139 0.090

Example 78, Comparative Example 78

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 49.

TABLE 49 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 78 BH-13 BD-1 150 0.139 0.090 Comp. Ex. 78 BH-13-aBD-1  83 0.139 0.090

Example 79, Comparative Example 79

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 50.

TABLE 50 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 79 BH-14 BD-1 100 0.139 0.090 Comp. Ex. 79 BH-14-aBD-1  63 0.139 0.090

Example 80, Comparative Example 80

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 51.

TABLE 51 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 80 BH-15 BD-1 100 0.139 0.090 Comp. Ex. 80 BH-15-aBD-1  60 0.139 0.090

Example 81, Comparative Example 81

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 52.

TABLE 52 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 81 BH-16 BD-1 158 0.139 0.090 Comp. Ex. 81 BH-1-cBD-1 103 0.139 0.090

Example 82, Comparative Example 82

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 53.

TABLE 53 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 82 BH-7 BD-2 98 0.140 0.080 Comp. Ex. 82 BH-7-aBD-2 64 0.140 0.080

Example 83, Comparative Example 83

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 54.

TABLE 54 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 83 BH-8 BD-2 100 0.140 0.080 Comp. Ex. 83 BH-8-aBD-2  64 0.140 0.080

Example 84, Comparative Example 84

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 55.

TABLE 55 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 84 BH-9 BD-2 94 0.140 0.080 Comp. Ex. 84 BH-9-aBD-2 58 0.140 0.080

Example 85, Comparative Example 85

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 56.

TABLE 56 Emitting layer Host Dopant LT95 Chromaticity material material(h) ClEx ClEy Example 85 BH-10 BD-2 83 0.140 0.081 Comp. Ex. 85 BH-10-aBD-2 50 0.140 0.080

Example 86, Comparative Example 86

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 57.

TABLE 57 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 86 BH-11 BD-2 73 0.140 0.080 Comp. Ex. 86BH-11-a BD-2 45 0.140 0.080

Example 87, Comparative Example 87

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 58.

TABLE 58 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 87 BH-12 BD-2 65 0.140 0.080 Comp. Ex. 87BH-12-a BD-2 40 0.140 0.080

Example 88, Comparative Example 88

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 59.

TABLE 59 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 88 BH-13 BD-2 127 0.140 0.080 Comp. Ex. 88BH-13-a BD-2  75 0.140 0.080

Example 89, Comparative Example 89

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 60.

TABLE 60 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 89 BH-14 BD-2 88 0.140 0.080 Comp. Ex. 89BH-14-a BD-2 54 0.140 0.080

Example 90, Comparative Example 90

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 61.

TABLE 61 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 90 BH-15 BD-2 84 0.140 0.080 Comp. Ex. 90BH-15-a BD-2 52 0.140 0.080

Example 91, Comparative Examples 91-1, 91-2 and 91-3

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 62.

TABLE 62 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 91 BH-16 BD-2 131 0.140 0.080 Comp. Ex. 91-1BH-1-a BD-2  83 0.140 0.080 Comp. Ex. 91-2 BH-1-b BD-2  84 0.140 0.080Comp. Ex. 91-3 BH-1-c BD-2  86 0.140 0.080

Example 92, Comparative Example 92

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 63.

TABLE 63 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 92 BH-7 BD-3 118 0.135 0.098 Comp. Ex. 92BH-7-a BD-3 75 0.135 0.098

Example 93, Comparative Example 93

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 64.

TABLE 64 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 93 BH-8 BD-3 112 0.135 0.098 Comp. Ex. 93BH-8-a BD-3  72 0.135 0.098

Example 94, Comparative Example 94

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 65.

TABLE 65 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 94 BH-9 BD-3 105 0.135 0.098 Comp. Ex. 94BH-9-a BD-3  66 0.135 0.098

Example 95, Comparative Example 95

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 66.

TABLE 66 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 95 BH-10 BD-3 90 0.135 0.098 Comp. Ex. 95BH-10-a BD-3 60 0.135 0.098

Example 96, Comparative Example 96

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 67.

TABLE 67 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 96 BH-11 BD-3 80 0.135 0.098 Comp. Ex. 96BH-11-a BD-3 53 0.135 0.098

Example 97, Comparative Example 97

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 68.

TABLE 68 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 97 BH-12 BD-3 70 0.135 0.098 Comp. Ex. 97BH-12-a BD-3 46 0.135 0.099

Example 98, Comparative Example 98

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 69.

TABLE 69 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 98 BH-13 BD-3 150 0.135 0.098 Comp. Ex. 98BH-13-a BD-3  92 0.135 0.098

Example 99, Comparative Example 99

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 70.

TABLE 70 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 99 BH-14 BD-3 102 0.135 0.098 Comp. Ex. 99BH-14-a BD-3  64 0.135 0.098

Example 100, Comparative Example 100

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 71.

TABLE 71 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 100 BH -15 BD-3 96 0.135 0.098 Comp. Ex. 100BH -15-a BD-3 60 0.135 0.098

Example 101, Comparative Examples 101-1, 101-2 and 101-3

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 72.

TABLE 72 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 101 BH-16 BD-3 157 0.135 0.098 Comp. Ex. 101-1BH-1-a BD-3 96 0.135 0.098 Comp. Ex. 101-2 BH-1-b BD-3 93 0.135 0.098Comp. Ex. 101-3 BH-1-c BD-3 100 0.135 0.098

Example 102, Comparative Example 102

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 73.

TABLE 73 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 102 BH-7 BD-4 126 0.135 0.086 Comp. Ex. 102BH-7-a BD-4  80 0.135 0.086

Example 103, Comparative Example 103

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 74.

TABLE 74 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 103 BH-8 BD-4 126 0.135 0.086 Comp. Ex. 103BH-8-a BD-4  76 0.135 0.086

Example 104, Comparative Example 104

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 75.

TABLE 75 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 104 BH-9 BD-4 110 0.135 0.085 Comp. Ex. 104BH-9-a BD-4  70 0.135 0.086

Example 105, Comparative Example 105

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 76.

TABLE 76 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 105 BH-10 BD-4 103 0.135 0.086 Comp. Ex. 105BH-10-a BD-4  60 0.135 0.086

Example 106, Comparative Example 106

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 77.

TABLE 77 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 106 BH-11 BD-4 90 0.135 0.086 Comp. Ex. 106BH-11-a BD-4 56 0.135 0.086

Example 107, Comparative Example 107

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 78.

TABLE 78 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 107 BH-12 BD-4 80 0.135 0.086 Comp. Ex. 107BH-12-a BD-4 50 0.135 0.086

Example 108, Comparative Example 108

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 79.

TABLE 79 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 108 BH-13 BD-4 157 0.135 0.085 Comp. Ex. 108BH-13-a BD-4  92 0.135 0.086

Example 109, Comparative Example 109

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 80.

TABLE 80 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 109 BH-14 BD-4 110 0.135 0.086 Comp. Ex. 109BH-14-a BD-4  65 0.135 0.086

Example 110, Comparative Example 110

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 81.

TABLE 81 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 110 BH-15 BD-4 100 0.135 0.086 Comp. Ex. 110BH-15-a BD-4  60 0.135 0.086

Example 111, Comparative Examples 111-1, 111-2 and 111-3

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 82.

TABLE 82 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 111 BH-16 BD-4 165 0.135 0.086 Comp. Ex. 111-1BH-1-a BD-4  98 0.135 0.086 Comp. Ex. 111-2 BH-1-b BD-4 100 0.135 0.086Comp. Ex. 111-3 BH-1-c BD-4 103 0.135 0.086

Example 112, Comparative Example 112

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 83.

TABLE 83 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 112 BH-7 BD-5 150 0.135 0.080 Comp. Ex. 112BH-7-a BD-5  90 0.135 0.080

Example 113, Comparative Example 113

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 84.

TABLE 84 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 113 BH-8 BD-5 155 0.135 0.080 Comp. Ex. 113BH-8-a BD-5  90 0.135 0.080

Example 114, Comparative Example 114

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 85.

TABLE 85 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 114 BH-9 BD-5 143 0.135 0.080 Comp. Ex. 114BH-9-a BD-5  88 0.135 0.080

Example 115, Comparative Example 115

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 86.

TABLE 86 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 115 BH-10 BD-5 124 0.135 0.080 Comp. Ex. 115BH-10-a BD-5  75 0.135 0.080

Example 116, Comparative Example 116

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 87.

TABLE 87 Emitting layer Chromaticity Host material Dopant materialLT95(h) ClEx ClEy Example 116 BH-11 BD-5 106 0.135 0.080 Comp. Ex. 116BH-11-a BD-5  68 0.135 0.080

Example 117, Comparative Example 117

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 88.

TABLE 88 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 117 BH-12 BD-5 90 0.135 0.081 Comp. Ex. 117BH-12-a BD-5 62 0.135 0.080

Example 118, Comparative Example 118

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 89.

TABLE 89 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 118 BH-13 BD-5 195 0.135 0.080 Comp. Ex. 118BH-13-a BD-5 117 0.135 0.080

Example 119, Comparative Example 119

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 90.

TABLE 90 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 119 BH-14 BD-5 138 0.135 0.080 Comp. Ex. 119BH-14-a BD-5  80 0.135 0.080

Example 120, Comparative Example 120

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 91.

TABLE 91 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 120 BH-15 BD-5 130 0.135 0.080 Comp. Ex. 120BH-15-a BD-5 77 0.135 0.080

Example 121, Comparative Examples 121-1, 121-2 and 121-3

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 92.

TABLE 92 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 121 BH-16 BD-5 200 0.135 0.080 Comp. Ex. 121-1BH-1-a BD-5 123 0.135 0.080 Comp. Ex. 121-2 BH-1-b BD-5 125 0.135 0.080Comp. Ex. 121-3 BH-1-c BD-5 135 0.135 0.080

Example 122, Comparative Example 122

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 93.

TABLE 93 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 122 BH-7 BD-6 190 0.136 0.090 Comp. Ex. 122BH-7-a BD-6 114 0.136 0.090

Example 123, Comparative Example 123

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 94.

TABLE 94 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 123 BH-8 BD-6 179 0.136 0.090 Comp. Ex. 123BH-8-a BD-6 110 0.136 0.090

Example 124, Comparative Example 124

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 95.

TABLE 95 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 124 BH-9 BD-6 164 0.136 0.090 Comp. Ex. 124BH-9-a BD-6  98 0.136 0.090

Example 125, Comparative Example 125

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 96.

TABLE 96 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 125 BH-10 BD-6 147 0.136 0.090 Comp. Ex. 125BH-10-a BD-6  88 0.136 0.090

Example 126, Comparative Example 126

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 97.

TABLE 97 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 126 BH-11 BD-6 122 0.136 0.090 Comp. Ex. 126BH-11-a BD-6  80 0.136 0.090

Example 127, Comparative Example 127

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 98.

TABLE 98 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 127 BH-12 BD-6 118 0.136 0.090 Comp. Ex. 127BH-12-a BD-6  72 0.136 0.090

Example 128, Comparative Example 128

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 99.

TABLE 99 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 128 BH-13 BD-6 242 0.136 0.090 Comp. Ex. 128BH-13-a BD-6 140 0.136 0.090

Example 129, Comparative Example 129

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 100.

TABLE 100 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 129 BH-14 BD-6 155 0.136 0.090 Comp. Ex. 129BH-14-a BD-6  92 0.136 0.090

Example 130, Comparative Example 130

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 101.

TABLE 101 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 130 BH-15 BD-6 146 0.136 0.090 Comp. Ex. 130BH-15-a BD-6  90 0.136 0.090

Example 131, Comparative Examples 131-1, 131-2 and 131-3

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 102.

TABLE 102 Emitting layer Host Chromaticity material Dopant materialLT95(h) CIEx CIEy Example 131 BH-16 BD-6 245 0.136 0.090 Comp. Ex. 131-1BH-1-a BD-6 146 0.136 0.090 Comp. Ex. 131-2 BH-1-b BD-6 142 0.136 0.090Comp. Ex. 131-3 BH-1-c BD-6 150 0.136 0.090

Example 132, Comparative Example 132

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 103.

TABLE 103 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 132 BH-7 BD-7 82 0.144 0.061 Comp. Ex. 132BH-7-a BD-7 50 0.144 0.061

Example 133, Comparative Example 133

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 104.

TABLE 104 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 133 BH-8 BD-7 82 0.144 0.061 Comp. Ex. 133BH-8-a BD-7 50 0.144 0.061

Example 134, Comparative Example 134

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 105.

TABLE 105 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 134 BH-9 BD-7 74 0.144 0.060 Comp. Ex. 134BH-9-a BD-7 48 0.144 0.060

Example 135, Comparative Example 135

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 106.

TABLE 106 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 135 BH-10 BD-7 63 0.144 0.061 Comp. Ex. 135BH-10-a BD-7 42 0.144 0.061

Example 136, Comparative Example 136

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 107.

TABLE 107 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 136 BH-11 BD-7 61 0.144 0.061 Comp. Ex. 136BH-11-a BD-7 37 0.144 0.061

Example 137, Comparative Example 137

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 108.

TABLE 108 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 137 BH-12 BD-7 55 0.144 0.061 Comp. Ex. 137BH-12-a BD-7 33 0.144 0.061

Example 138, Comparative Example 138

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 109.

TABLE 109 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 138 BH-13 BD-7 105 0.144 0.060 Comp. Ex. 138BH-13-a BD-7 65 0.144 0.061

Example 139, Comparative Example 139

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 110.

TABLE 110 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 139 BH-14 BD-7 75 0.144 0.061 Comp. Ex. 139BH-14-a BD-7 45 0.144 0.061

Example 140, Comparative Example 140

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 111.

TABLE 111 Emitting layer Chromaticity Host material Dopant materialLT95(h) CIEx CIEy Example 140 BH-15 BD-7 70 0.144 0.061 Comp. Ex. 140BH-15-a BD-7 43 0.144 0.061

Example 141, Comparative Examples 141-1, 141-2 and 141-3

Except that the compounds shown in the following table were used as thehost material and the dopant material of the emitting layer, the organicEL devices were fabricated and evaluated in the same manner as inExample 1. The results are shown in Table 112.

TABLE 112 Emitting layer Chromaticity Host material Dopant materialL195(H) CIEx CIEy Example 141 BH-16 BD-7 107  0.144 0.061 Comp. Ex.141-1 BH-1-a BD-7 65 0.144 0.061 Comp. Ex. 141-2 BH-1-b BD-7 66 0.1440.061 Comp. Ex. 141-3 BH-1-c BD-7 72 0.144 0.061

From the results of Tables 1 to 112, it can be recognized that, if thecompound of the invention having a deuterium atom at the particularposition is used in the emitting layer of the organic EL device, thelifetime of the organic EL device is prolonged compared with the casewhere the compound having no deuterium atom at the particular positionis used. Moreover, comparison between Example 4 and Comparative Example4-2 shows that even in compound having deuterium atom at a particularsite, the driving voltages of organic EL device can be lowered byemploying the structure of the invention.

Several embodiments and/or examples of the present invention have beendescribed in detail above. However, without substantially departing fromnovel teachings and effects of the present invention, the person skilledin the art can readily make a number of modifications to the embodimentsand/or examples which are exemplifications of these teachings andeffects. Thus, these modifications are included in the scope of thepresent invention.

1. A compound represented by the following formula (1):

wherein in the formula (1), R₁ to R₈ and R₁₁ to R₁₄ are independently ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted aryl group having 6 to 50ring carbon atoms, or a substituted or unsubstituted monovalentheterocyclic group having 5 to 50 ring atoms; R₁₅ to R₁₆ and R₁₈ arehydrogen atoms; at least one of R₁ to R₈ is a deuterium atom; two ormore adjacent groups of R₁ to R₄, two or more adjacent groups of R₅ toR₈ and two or more adjacent groups of R₁₁ to R₁₄ do not form a ring; L₁and L₂ are independently a single bond, a substituted or unsubstitutedarylene group having 6 to 30 ring carbon atoms, or a substituted orunsubstituted divalent heterocyclic group having 5 to 30 ring atoms; Aris a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or a substituted or unsubstituted monovalent heterocyclic grouphaving 5 to 50 ring atoms.
 2. The compound according to claim 1, whereinAr is a group represented by the following formula (a2):

wherein in the formula (a2), is a single bond bonding to L₁; R₂₁ is asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or a substituted or unsubstituted monovalent heterocyclic grouphaving 5 to 50 ring atoms; m1 is an integer of 0 to 4; m2 is an integerof 0 to 5; when each of m1 to m2 is 2 or more, the plural R₂₁s may bethe same or different; and when each of m1 to m2 is 2 or more, adjacentplural R₂₁s are bonded with each other to form a substituted orunsubstituted, saturated or unsaturated ring, or do not form asubstituted or unsubstituted, saturated or unsaturated ring.
 3. Thecompound according to claim 1, wherein Ar is p-biphenyl group,m-biphenyl group, or o-biphenyl group.
 4. The compound according toclaim 1, wherein at least one of R₁₁ to R₁₆ and R₁₈ is a deuterium atom.5. The compound according to claim 1, wherein all of R₁₁ to R₁₆ and R₁₈are deuterium atoms.
 6. The compound according to claim 1, wherein allhydrogen atoms possessed by Ar are protium atoms; all hydrogen atomspossessed by L₁ and L₂ in the case when L₁ and L₂ are a substituted orunsubstituted arylene group having 6 to 30 ring carbon atoms, or asubstituted or unsubstituted divalent heterocyclic group having 5 to 30ring atoms are protium atoms; and all of R₁₁ to R₁₆ and R₁₈ which arehydrogen atoms are protium atoms.
 7. The compound according to claim 1,wherein L₂ is a single bond.
 8. The compound according to claim 1,wherein at least one hydrogen atom possessed by -L₁-Ar is a deuteriumatom.
 9. The compound according to claim 1, wherein all hydrogen atomspossessed by -L₁-Ar are deuterium atoms.
 10. The compound according toclaim 1, wherein L₁ is a single bond.
 11. The compound according toclaim 1, wherein the compound represented by the formula (1) is selectedfrom the group consisting of compounds represented by each of thefollowing formulas:


12. The compound according to claim 1, wherein the compound representedby the formula (1) is selected from the group consisting of compoundsrepresented by each of the following formulas:


13. The compound according to claim 1, wherein the compound representedby the formula (1) is selected from the group consisting of compoundsrepresented by each of the following formulas:


14. A composition comprising the compound according to claim 1, whereinthe content ratio of a protium compound having the same structure asformula (1) except that only protium atoms are contained as hydrogenatoms to the total of the compound represented by formula (1) and theprotium compound is 99 mol % or less.
 15. The composition according toclaim 14, wherein the content ratio of the compound represented byformula (1) to the total of the compound represented by the formula (1)and the protium compound is 30 mol % or more.
 16. An organicelectroluminesoence device comprising: a cathode, an anode, and one ortwo or more organic layer disposed between the cathode and the anode,wherein at least one organic layer is an emitting layer, and at leastone layer of the emitting layer comprises the compound according toclaim 1 or the composition comprising the compound represented by theformula (1) and a protium compound having the same structure as formula(1) except that only protium atoms are contained as hydrogen atoms,wherein the content ratio of the protium compound to the total of thecompound represented by formula (1) and the protium compound is 99 mol %or less.
 17. The organic electroluminescence device according to claim16, wherein in the formula (1), all hydrogen atoms possessed by Ar areprotium atoms; all hydrogen atoms possessed by L₁ and L₂ in the casewhen L₁ and L₂ are a substituted or unsubstituted arylene group having 6to 30 ring carbon atoms, or a substituted or unsubstituted divalentheterocyclic group having 5 to 30 ring atoms are protium atoms; and allof R₁₁ to R₁₆ and R₁₈ which are hydrogen atoms are protium atoms. 18.The organic electroluminescence device according to claim 16, wherein inthe formula (1), at least one hydrogen atom possessed by -L₁-Ar is adeuterium atom; all hydrogen atoms possessed by L₂ in the case when L₂is a substituted or unsubstituted arylene group having 6 to 30 ringcarbon atoms, or a substituted or unsubstituted divalent heterocyclicgroup having 5 to 30 ring atoms are protium atoms; and all of R₁₁ to R₁₆and R₁₈ which are hydrogen atoms are protium atoms.
 19. The organicelectroluminescence device according to claim 16, wherein in the formula(1), all hydrogen atoms possessed by -L₁-Ar are protium atoms; and atleast one of R₁₁ to R₁₆ and R₁₈ which are hydrogen atoms and hydrogenatoms possessed by L₂ is a deuterium atom.
 20. The organicelectroluminescence device according to claim 16, wherein in the formula(1), at least one hydrogen atom possessed by -L₁-Ar is a protium atom;and at least one of R₁₁ to R₁₆ and R₁₈ which are hydrogen atoms andhydrogen atoms possessed by L₂ is a deuterium atom.
 21. The organicelectroluminescence device according to claim 16, wherein the emittinglayer further comprises a compound represented by the following formula(41):

wherein, in the formula (41), a ring, b ring and c ring areindependently a substituted or unsubstituted aromatic hydrocarbon ringhaving 6 to 50 ring carbon atoms, or a substituted or unsubstitutedheterocyclic ring having 5 to 50 ring atoms; R₄₀₁ and R₄₀₂ areindependently bonded to the a ring, the b ring or the c ring to form asubstituted or unsubstituted heterocyclic ring or do not form asubstituted or unsubstituted heterocyclic ring; R₄₀₁ and R₄₀₂ that donot form the substituted or unsubstituted heterocyclic ring areindependently a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted alkenyl group having 2 to50 carbon atoms, a substituted or unsubstituted alkynyl group having 2to 50 carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving 3 to 50 ring carbon atoms, a substituted or unsubstituted arylgroup having 6 to 50 ring carbon atoms, or a substituted orunsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;22. The organic electroluminescence device according to claim 16,comprising a hole-transporting layer between the anode and the emittinglayer, wherein the hole-transporting layer comprises the followingcompound HT-2.